JPH026353B2 - - Google Patents
Info
- Publication number
- JPH026353B2 JPH026353B2 JP19485581A JP19485581A JPH026353B2 JP H026353 B2 JPH026353 B2 JP H026353B2 JP 19485581 A JP19485581 A JP 19485581A JP 19485581 A JP19485581 A JP 19485581A JP H026353 B2 JPH026353 B2 JP H026353B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- under reduced
- reduced pressure
- organic layer
- diphenylethylamine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 8
- -1 N-(2-benzylthioethyl)-1,2-diphenylethylamine Chemical compound 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- UOULCEYHQNCFFH-UHFFFAOYSA-M sodium;hydroxymethanesulfonate Chemical compound [Na+].OCS([O-])(=O)=O UOULCEYHQNCFFH-UHFFFAOYSA-M 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- DTGGNTMERRTPLR-CQSZACIVSA-N (1r)-1,2-diphenylethanamine Chemical compound C([C@@H](N)C=1C=CC=CC=1)C1=CC=CC=C1 DTGGNTMERRTPLR-CQSZACIVSA-N 0.000 description 1
- OTKCEEWUXHVZQI-UHFFFAOYSA-N 1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=C1 OTKCEEWUXHVZQI-UHFFFAOYSA-N 0.000 description 1
- RXMTUVIKZRXSSM-UHFFFAOYSA-N 2,2-diphenylethanamine Chemical compound C=1C=CC=CC=1C(CN)C1=CC=CC=C1 RXMTUVIKZRXSSM-UHFFFAOYSA-N 0.000 description 1
- DVXJHLBTPJVZEA-UHFFFAOYSA-N 2-benzylsulfanylacetaldehyde Chemical compound O=CCSCC1=CC=CC=C1 DVXJHLBTPJVZEA-UHFFFAOYSA-N 0.000 description 1
- XZXIWQYIVDFDSP-UHFFFAOYSA-N 2-benzylsulfanylethanamine;hydrochloride Chemical compound [Cl-].[NH3+]CCSCC1=CC=CC=C1 XZXIWQYIVDFDSP-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- GRWIABMEEKERFV-UHFFFAOYSA-N methanol;oxolane Chemical compound OC.C1CCOC1 GRWIABMEEKERFV-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
本発明は下記一般式〔〕で表わされる化合物
およびその塩類に関する。
〔式中、R1およびR2は水素原子を示す。以下同
じ。〕
本発明化合物〔〕は解熱、鎮痛および消炎剤
として有用な化合物であり、本発明の目的は価値
ある薬理学的性質を有する化合物を提供するにあ
る。
本発明化合物〔〕は例えば下記の(A)、(B)の方
法で合成することができる。
〔式中、R3はベンジル基、アセチル基またはベ
ンゾイル基を示す。以下同じ。〕
上記(A)、(B)の反応式中、還元剤として
NaBH3CNを用いると好収率で目的物を得るが、
ラネーニツケルを触媒として水素化を行つてもよ
い。本発明化合物〔〕は不整炭素が１つある。
それ故本発明化合物〔〕には光学異性体が存在
するが、それらはいずれも本発明の範囲に包含さ
れる。本発明化合物〔〕が光学活性化合物であ
る場合は上記反応式の内(B)の方法を用いる。
上記の方法により合成した本発明化合物〔〕
は酸付加塩の形態とすることができ、酸付加塩は
無機酸もしくは有機酸を使用して常法により得る
ことができる。本発明化合物の医薬として許容さ
れる塩を形成する適当な酸の例は、塩酸、硫酸、
燐酸、乳酸、マレイン酸、フマル酸、メタンスル
ホン酸、パラトルエンスルホン酸などである。
以下に参考例および実施例を示す。
参考例 １
Ｎ−（２−ベンジルチオエチル）−１，２−ジフ
エニルエチルアミンの製造
デソキシベンゾイン（9.81ｇ）およびＳ−ベン
ジルシステアミン塩酸塩（30.5ｇ）のメタノール
（150ml）溶液にNaBH3CH（2.20ｇ）およびモレ
キユラーシーブス3A（10ｇ）を加え室温で１週間
撹拌する。反応液にＮ NaOH（80ml）を加え減
圧濃縮する。濃縮液に水（50ml）およびクロロホ
ルム（300ml）を加え有機層を分取する。有機層
を飽和食塩水で洗浄後無水硫酸マグネシウムで乾
燥する。溶媒を減圧留去し得られる油状物をシリ
カゲルカラムクロマトで精製し標記化合物12.5ｇ
（収率72％）を得る。
IR（neat、cm-1）
1600、1495、1455
NMR（CDCl3、δ）
1.72（1H、ｓ、−ＮＨ−）、2.30〜2.63（4H、ｍ、
−SCH2 ＣH2 NH−）、2.87（2H、ｄ、Ｊ＝7.0Hz、
−ＣH2 CH）、3.50（2H、ｓ、−SCH2 C6H5）、
3.77（1H、dd、Ｊ＝7.0、6.0Hz、−CH2CＨ）、
6.87〜7.37（15H、ｍ、アロマチツクＨ）
参考例 ２
Ｎ−（２−ベンジルチオエチル）−１，２−ジフ
エニルエチルアミン塩酸塩の製造
Ｎ−（２−ベンジルチオエチル）−１，２−ジフ
エニルエチルアミン（0.50ｇ）を酢酸エチルに溶
解し、1.5N塩酸／酢酸エチル（1.0ml）を加え析
出する結晶を取し標記化合物0.40ｇ（77％）を
得る。
融点179〜180℃
IR（KBr、cm-1）
1590、1580、1490、1450
NMR（DMSO−d6、δ）
2.60〜3.07（4H、ｍ、−SCH2 ＣH2 NH−）、3.07
〜3.43（2H、ｍ、−ＣH2 CH）、3.60（2H、ｓ、−
SCH2 C6H5）、4.13〜4.67（2H、ｍ、−CH2CＨ）、
6.80〜7.60（15H、ｍ、アロマチツクＨ）、9.33〜
10.67（2H、br、−ＮＨ−及びＨCl）
参考例 ３
Ｎ−（２−メルカプトエチル）−１，２−ジフエ
ニルエチルアミンの製造
Ｎ−（２−ベンジルチオエチル）−１，２−ジフ
エニルエチルアミン（6.0ｇ）をTHF（20ml）お
よび液体アンモニア（80ml）の混液に溶解し、金
属ナトリウム（1.0ｇ）を少量ずつ加える。反応
終了後、液体アンモニアを留去する。残査に、水
およびクロロホルムを加え、有機層を分取する。
有機層を飽和食塩水で洗浄後、無水硫酸マグネシ
ウムで乾燥する。溶媒を減圧留去し標記化合物
4.6ｇ（定量的）を得る。
IR（neat、cm-1）
1600、1490、1450、755、700
NMR（CDCl3、δ）
1.17〜2.10（2H、br、−ＮＨ−および−ＳＨ）、
2.27〜2.70（4H、ｍ、−SCH2 ＣH2 NH−）、2.73〜
3.07（2H、ｍ、−ＣH2 CH）、3.78（2H、ddd、Ｊ
＝7.0、6.0、2.0Hz、−CH2CＨ）、6.87〜7.53
（10H、ｍ、アロマチツクＨ）
参考例 ４
Ｎ−（２−メルカプトエチル）−１，２−ジフエ
ニルエチルアミン塩酸塩の製造
Ｎ−（２メルカプトエチル）−１，２−ジフエニ
ルエチルアミン（0.50ｇ）を用い実施例３と同様
に操作して標記化合物0.42ｇ（74％）を得る。
融点247〜250℃（分解）
IR（KBr、cm-1）
1570、1500、1455、700
NMR（DMSO−d6、δ）
2.63〜3.93（7H、ｍ、ＨSCH2 ＣH2 Ｎ及び−
ＣH2 CH）、4.23〜4.83（1H、ｍ、−CH2CＨ）、
6.83〜7.73（10H、ｍ、アロマチツクＨ）、9.53〜
10.73（2H、br、−ＮＨ−及びＨCl）
参考例 ５
（1R）−Ｎ−（２−ベンジルチオエチル）−１，
２−ジフエニルエチルアミンの製造
（ベンジルチオ）アセトアルデヒド（1.7ｇ）
および（1R）−１，２−ジフエニルエチルアミン
（11.8ｇ）のメタノール−THF1：１（40ml）溶液
に5N−メタノール−塩酸（４ml）、モレキユラー
シーブス3A（2.0ｇ）およびNaBH3CN（0.38ｇ）
を加え室温で３日間撹拌する。反応液にＮ−
NaOHを加えアルカリ性とした後、減圧濃縮す
る。残査に酢酸エチルおよび水を加え、有機層を
分取する。有機層を飽和食塩水で洗浄後無水硫酸
マグネシウムで乾燥する。溶媒を減圧留去し残査
をシリカゲルカラムクロマトで精製し標記化合物
1.7ｇ（50％）を得る。
実施例 １
３−（１，２−ジフエニルエチル）チアゾリジ
ンの製造
Ｎ−（２−メルカプトエチル）−１，２−ジフエ
ニルエチルアミン（2.57ｇ）をメタノール（50
ml）および水（25ml）の混液に溶解し、ヒドロキ
シメタンスルホン酸ナトリウム（7.6ｇ）を加え
３時間還流する。放冷後、減圧濃縮し、残査に水
およびクロロホルムを加え、有機層を分取する。
有機層を飽和食塩水で洗浄後、無水硫酸マグネシ
ウムで乾燥する。溶媒を減圧濃縮し、標記化合物
1.38ｇ（51％）を得る。
融点93℃（酢酸エチル）
IR（KBr、cm-1）
1600、1490、1440、1305、1220
NMR（CDCl3、δ）
2.67〜3.30（4H、ｍ、−SCH2 ＣH2 Ｎ）、2.90
（1H、dd、Ｊ＝13.0、9.5Hz、
The present invention relates to compounds represented by the following general formula [] and salts thereof. [In the formula, R 1 and R 2 represent hydrogen atoms. same as below. ] The compound of the present invention [ ] is a compound useful as an antipyretic, analgesic, and antiinflammatory agent, and an object of the present invention is to provide a compound having valuable pharmacological properties. The compound of the present invention [] can be synthesized, for example, by the following methods (A) and (B). [In the formula, R 3 represents a benzyl group, an acetyl group, or a benzoyl group. same as below. ] In the reaction formulas (A) and (B) above, as a reducing agent
When using NaBH 3 CN, the desired product can be obtained in good yield, but
Hydrogenation may be carried out using Raney nickel as a catalyst. The compound of the present invention [ ] has one asymmetric carbon.
Therefore, although the compound of the present invention [] has optical isomers, all of them are included within the scope of the present invention. When the compound of the present invention [] is an optically active compound, method (B) of the above reaction formula is used. Compound of the present invention synthesized by the above method []
can be in the form of an acid addition salt, which can be obtained by conventional methods using inorganic or organic acids. Examples of suitable acids for forming pharmaceutically acceptable salts of compounds of the invention include hydrochloric acid, sulfuric acid,
These include phosphoric acid, lactic acid, maleic acid, fumaric acid, methanesulfonic acid, and para-toluenesulfonic acid. Reference examples and examples are shown below. Reference Example 1 Production of N-(2-benzylthioethyl)-1,2-diphenylethylamine A methanol (150 ml) solution of desoxybenzoin (9.81 g) and S-benzylcysteamine hydrochloride (30.5 g) was added with NaBH 3 (2.20 g) and Molecular Sieves 3A (10 g) were added and stirred at room temperature for one week. Add N NaOH (80 ml) to the reaction solution and concentrate under reduced pressure. Add water (50 ml) and chloroform (300 ml) to the concentrate and separate the organic layer. The organic layer is washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting oil was purified using silica gel column chromatography to obtain 12.5 g of the title compound.
(yield 72%). IR (neat, cm -1 ) 1600, 1495, 1455 NMR (CDCl 3 , δ) 1.72 (1H, s, -NH -), 2.30-2.63 (4H, m,
−SC H 2 C H 2 NH−), 2.87 (2H, d, J = 7.0Hz,
-C H 2 CH), 3.50 (2H, s, -S H 2 C 6 H 5 ),
3.77 (1H, dd, J=7.0 , 6.0Hz, -CH2CH ),
6.87-7.37 (15H, m, aromatic H) Reference example 2 Production of N-(2-benzylthioethyl)-1,2-diphenylethylamine hydrochloride N-(2-benzylthioethyl)-1,2-diphenyl Enylethylamine (0.50 g) was dissolved in ethyl acetate, 1.5N hydrochloric acid/ethyl acetate (1.0 ml) was added, and the precipitated crystals were collected to obtain 0.40 g (77%) of the title compound. Melting point 179-180℃ IR (KBr, cm -1 ) 1590, 1580, 1490, 1450 NMR (DMSO-d 6 , δ) 2.60-3.07 (4H, m, -SC H 2 C H 2 NH-), 3.07
~3.43 (2H, m, -C H 2 CH), 3.60 (2H, s, -
SC H 2 C 6 H 5 ), 4.13-4.67 (2H, m, -CH 2 C H ),
6.80~7.60 (15H, m, aromatic H), 9.33~
10.67 (2H, br, -N H - and H Cl) Reference Example 3 Production of N-(2-mercaptoethyl)-1,2-diphenylethylamine N-(2-benzylthioethyl)-1,2-diphenylamine Enylethylamine (6.0 g) is dissolved in a mixture of THF (20 ml) and liquid ammonia (80 ml) and sodium metal (1.0 g) is added in portions. After the reaction is complete, liquid ammonia is distilled off. Water and chloroform are added to the residue, and the organic layer is separated.
The organic layer is washed with saturated brine and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound.
Obtain 4.6 g (quantitative). IR (neat, cm -1 ) 1600, 1490, 1450, 755, 700 NMR ( CDCl3 , δ) 1.17-2.10 (2H, br, -NH- and -SH ),
2.27~2.70 (4H, m, -SC H2CH2NH- ), 2.73 ~
3.07 (2H, m, -C H 2 CH), 3.78 (2H, ddd, J
=7.0, 6.0, 2.0Hz, -CH2CH ), 6.87 ~ 7.53
(10H, m, aromatic H) Reference example 4 Production of N-(2-mercaptoethyl)-1,2-diphenylethylamine hydrochloride N-(2-mercaptoethyl)-1,2-diphenylethylamine (0.50 g) 0.42 g (74%) of the title compound was obtained by the same procedure as in Example 3. Melting point 247-250℃ (decomposed) IR (KBr, cm -1 ) 1570, 1500, 1455, 700 NMR (DMSO-d 6 , δ) 2.63-3.93 (7H, m, H SC H 2 C H 2 N and -
CH2CH ), 4.23-4.83 (1H, m, -CH2CH ),
6.83~7.73 (10H, m, aromatic H), 9.53~
10.73 (2H, br, -N H - and H Cl) Reference example 5 (1R) -N-(2-benzylthioethyl)-1,
Production of 2-diphenylethylamine (benzylthio)acetaldehyde (1.7g)
and (1R)-1,2-diphenylethylamine (11.8 g) in methanol-THF 1:1 (40 ml), 5N-methanol-hydrochloric acid (4 ml), molecular sieves 3A (2.0 g) and NaBH 3 CN ( 0.38g)
and stirred at room temperature for 3 days. N- in the reaction solution
After making it alkaline by adding NaOH, it is concentrated under reduced pressure. Ethyl acetate and water are added to the residue, and the organic layer is separated. The organic layer is washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound.
Obtain 1.7g (50%). Example 1 Production of 3-(1,2-diphenylethyl)thiazolidine N-(2-mercaptoethyl)-1,2-diphenylethylamine (2.57 g) was dissolved in methanol (50 g).
ml) and water (25 ml), add sodium hydroxymethanesulfonate (7.6 g), and reflux for 3 hours. After cooling, it is concentrated under reduced pressure, water and chloroform are added to the residue, and the organic layer is separated.
The organic layer is washed with saturated brine and then dried over anhydrous magnesium sulfate. Concentrate the solvent under reduced pressure to obtain the title compound.
Obtain 1.38g (51%). Melting point 93℃ (ethyl acetate) IR (KBr, cm -1 ) 1600, 1490, 1440, 1305, 1220 NMR (CDCl 3 , δ) 2.67-3.30 (4H, m, -SC H 2 C H 2 N), 2.90
(1H, dd, J=13.0, 9.5Hz,
【式】）、
3.27（1H、dd、Ｊ＝13.0、4.0Hz、
[Formula]), 3.27 (1H, dd, J=13.0, 4.0Hz,
【式】）、3.63（1H、dd、Ｊ＝9.5、4.0
Hz、−CH2CＨ）、4.00及び4.20（2H、ABq、Ｊ
＝9.0Hz、−SCH2 Ｎ）、6.67〜7.33（10H、ｍ、ア
ロマチツクＨ）
実施例 ２
３−（１，２−ジフエニルエチル）チアゾリジ
ン塩酸塩の製造
３−（１，２−ジフエニルエチル）チアゾリジ
ン（1.0ｇ）をメタノール（８ml）とクロロホル
ム（４ml）の混液に溶解し、7.4Nメタノール−
塩酸（0.7ml）を加える。反応液を減圧濃縮し標
記化合物0.82ｇ（72％）を得る。
融点216〜217℃分解（メタノール）
IR（KBr、cm-1）
1605、1495、1450、1425、1205
NMR（DMSO−d6）
3.00〜4.05（6H、ｍ、−SCH2 ＣH2 Ｎ及び−Ｃ
H2CH）、4.08〜4.58（2H、ｍ、−SCH2 Ｎ）、
4.80（1H、dd、Ｊ＝9.5、4.0Hz、−CH2CＨ）、
6.83〜7.80（10H、ｍ、アロマチツクＨ）
実施例 ３
３−〔（1R）−１，２−ジフエニルエチル〕チア
ゾリジンの製造
（1R）−Ｎ−（２−メルカプトエチル）−１，２
−ジフエニルエチルアミン（1.3ｇ）をメタノー
ル（25ml）および水（12ml）の混液に溶解し、ヒ
ドロキシメタンスルホン酸ナトリウム（3.8ｇ）
を加え３時間還流する。放冷後、減圧濃縮し残査
に水およびクロロホルムを加え、有機層を分取す
る。有機層を飽和食塩水で洗浄後、無水硫酸マグ
ネシウムで乾燥する。溶媒を減圧濃縮し標記化合
物0.84ｇ（62％）を得る。 [Formula]), 3.63 (1H, dd, J = 9.5, 4.0 Hz, -CH 2 C H ), 4.00 and 4.20 (2H, ABq, J
=9.0Hz, -SCH2N ), 6.67-7.33 (10H, m, aromatic H) Example 2 Production of 3-(1,2-diphenylethyl)thiazolidine hydrochloride 3-(1,2-diphenylethyl)thiazolidine ( 1.0g) was dissolved in a mixture of methanol (8ml) and chloroform (4ml), and 7.4N methanol-
Add hydrochloric acid (0.7ml). The reaction solution was concentrated under reduced pressure to obtain 0.82 g (72%) of the title compound. Melting point 216-217℃ Decomposition (methanol) IR (KBr, cm -1 ) 1605, 1495, 1450, 1425, 1205 NMR (DMSO-d 6 ) 3.00-4.05 (6H, m, -SC H 2 C H 2 N and -C
H 2 CH), 4.08-4.58 (2H, m, -SC H 2 N),
4.80 (1H, dd, J=9.5 , 4.0Hz, -CH2CH ),
6.83-7.80 (10H, m, aromatic H) Example 3 Production of 3-[(1R)-1,2-diphenylethyl]thiazolidine (1R)-N-(2-mercaptoethyl)-1,2
- Dissolve diphenylethylamine (1.3 g) in a mixture of methanol (25 ml) and water (12 ml) and add sodium hydroxymethanesulfonate (3.8 g) to the solution.
and reflux for 3 hours. After cooling, it is concentrated under reduced pressure, water and chloroform are added to the residue, and the organic layer is separated. The organic layer is washed with saturated brine and then dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure to obtain 0.84 g (62%) of the title compound.
Claims (1)
その塩類。 〔式中、R1およびR2は水素原子を示す。〕[Claims] 1. Compounds represented by the following general formula [] and salts thereof. [In the formula, R 1 and R 2 represent hydrogen atoms. ]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56194855A JPS5896078A (en) | 1981-12-02 | 1981-12-02 | 3-aralkylthiazolidine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56194855A JPS5896078A (en) | 1981-12-02 | 1981-12-02 | 3-aralkylthiazolidine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5896078A JPS5896078A (en) | 1983-06-07 |
| JPH026353B2 true JPH026353B2 (en) | 1990-02-08 |
Family
ID=16331399
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56194855A Granted JPS5896078A (en) | 1981-12-02 | 1981-12-02 | 3-aralkylthiazolidine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5896078A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2825758B2 (en) * | 1994-06-03 | 1998-11-18 | クリンテック株式会社 | Nose heat mask |
-
1981
- 1981-12-02 JP JP56194855A patent/JPS5896078A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5896078A (en) | 1983-06-07 |
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