JPS6039068B2 - Synthesis method of 5-alkylamino-P-menthen-1 - Google Patents
Synthesis method of 5-alkylamino-P-menthen-1Info
- Publication number
- JPS6039068B2 JPS6039068B2 JP11692175A JP11692175A JPS6039068B2 JP S6039068 B2 JPS6039068 B2 JP S6039068B2 JP 11692175 A JP11692175 A JP 11692175A JP 11692175 A JP11692175 A JP 11692175A JP S6039068 B2 JPS6039068 B2 JP S6039068B2
- Authority
- JP
- Japan
- Prior art keywords
- alkylamino
- methylbutylidene
- alkylamine
- reaction
- reacted
- 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
- 238000001308 synthesis method Methods 0.000 title claims 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 18
- 150000004705 aldimines Chemical class 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- JKXQKGNGJVZKFA-UHFFFAOYSA-N 1-chloro-3-methylbut-2-ene Chemical compound CC(C)=CCCl JKXQKGNGJVZKFA-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 230000002194 synthesizing effect Effects 0.000 claims description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 150000003973 alkyl amines Chemical class 0.000 description 5
- FQNODTJXVHJRNF-UHFFFAOYSA-N CC(C)CC=NC(C)(C)C Chemical compound CC(C)CC=NC(C)(C)C FQNODTJXVHJRNF-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- 240000008564 Boehmeria nivea Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- -1 around 40 to 5 Chemical compound 0.000 description 1
- ANUZKYYBDVLEEI-UHFFFAOYSA-N butane;hexane;lithium Chemical compound [Li]CCCC.CCCCCC ANUZKYYBDVLEEI-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明は、Ｎ−（３ーメチルブチリデン）アルキルアミ
ンを出発物質とし、ラバンジュラールアルドィミドのカ
ルバニオンを経過する５−ァルキルアミノーＰ−メンテ
ンー１の合成法に関するものであり、このカルバニオン
を経過するには、出発物質にプレニルクロラィドを反応
させる方法と、ィソプレンを反応させる方法とがある。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for synthesizing 5-alkylamino-P-menthene-1 using N-(3-methylbutylidene)alkylamine as a starting material and proceeding through the carbanion of labandural aldimide. There are two methods for converting the carbanion: one is to react the starting material with prenyl chloride, and the other is to react with isoprene.
すなわち、Ｎ−（３−メチルブチリデン）ーアルキルア
ミンを原料とし、プレニルクロラィドをリチウムジァル
キルアミドの存在下に反応してジヒドロラバンジュラー
ルアルドィミンを高収率で得、このアルドィミンとアル
カリ金属とからラバンジュラールアルドィミンのカルバ
ニオンを経過して５−アルキルアミノ−Ｐーメンテン−
１とするか、またはＮ一（３ーメチルブチリデン）ーア
ルキルアミンとィソプレンとをアルカリ金属とからラバ
ンジユラールアルドイミンのカルバニオンを経過して５
−アルキルァミノーＰーメンテンー１を得るもので共に
高収率で選択的に目的物を得ることができる。本発明の
反応過程を示せば次のようになる。That is, using N-(3-methylbutylidene)-alkylamine as a raw material, prenyl chloride is reacted in the presence of lithium dialkylamide to obtain dihydrolavandural aldimine in high yield, and this aldimine and an alkali are reacted. 5-alkylamino-P-menthene through the carbanion of labandural aldimine from the metal
1 or by converting N-(3-methylbutylidene)-alkylamine and isoprene from an alkali metal to the carbanion of lavandural aldimine to 5.
-Alkylamino P-menthene-1 can be obtained selectively in high yield. The reaction process of the present invention is as follows.
本発明をプレニルクロラィドを使用する経路かな説明す
る。実施例１のように、Ｎ−（３−メチルブチリデン）
アルキルアミンを一１ぷ○のような低温でリチウムジア
ルキルアミドと混合し、次いでこれにプレニルクロラィ
ドを低温で反応させるとジヒドロラバンジユラールアル
ドイミンであるＮ一〔２−イソプロピルー５ーメチルー
４−へキセニリデン〕ァルキルアミンを生成する。The present invention will be described using a route using prenyl chloride. As in Example 1, N-(3-methylbutylidene)
When an alkylamine is mixed with a lithium dialkylamide at a low temperature such as 11 P○, and then reacted with prenyl chloride at a low temperature, dihydrolavanduralaldimine is obtained, N-[2-isopropyl-5-methyl-4 -Hexenylidene]alkylamine is produced.
このジヒドロラバンジュラールアルドイミンを金属アル
カリと反応させると、ジヒドロラバンジュラールアルド
イミンのカルバニオンを経過して環化し５ーアルキルァ
ミノーパラメンテン−１を生成する。反応させるプレニ
ルクロラィドは、Ｎ−（３ーメチルブチリデン）−アル
キルアミンに対し、当モル以上好ましくは２モルの比で
低温で反応させる。When this dihydrolavandural aldimine is reacted with a metal alkali, the carbanion of the dihydrolavandular aldimine is cyclized to produce 5-alkylaminoparamenthene-1. Prenyl chloride is reacted with N-(3-methylbutylidene)-alkylamine at a low temperature in a molar ratio of equal to or more, preferably 2 molar.
この際使用される触媒としてのりチウムジアルキルアミ
ドは、そのアルキル基としてはプチル、プロピル、エチ
ル等の低級アルキル基よりなるものが使用でき、炭化水
素、エーテル等の不活性溶媒の存在下に反応させること
が好ましい。次いで得られたジヒドロラバンジュラール
アルドィミンを金属アルカリと反応させてカルバニオン
を経過して環化し５−アルキルアミノ−Ｐ−メンテン−
１を得るには、ベンゼン等の溶媒中でその沸点以下、特
には５０００附近での反応が好ましく、更には少量のィ
ソプレンを併用するとアルカリ金属の作用が促進される
。反応終了後は禾反応原料・溶媒等を回収し、蒸留その
他の方法で、目的物たる５−アルキルアミノ−Ｐ−メン
テン−１を取得すればよい。次にＮ−（３ーメチルブチ
リデン）−アルキルアミンとイソプレンとからの経路に
よる５ーアルキルアミノ−Ｐーメンテンー１の合成法に
つき説明する。The alkyl group of the lithium dialkylamide used as a catalyst in this case can be a lower alkyl group such as butyl, propyl, ethyl, etc., and the reaction is carried out in the presence of an inert solvent such as a hydrocarbon or ether. It is preferable. Next, the obtained dihydroravandural aldimine is reacted with a metal alkali to undergo carbanion and cyclization to form 5-alkylamino-P-menthene-
In order to obtain 1, it is preferable to carry out the reaction in a solvent such as benzene at a temperature below its boiling point, particularly around 5000, and furthermore, when a small amount of isoprene is used in combination, the action of the alkali metal is accelerated. After the reaction is completed, the reaction raw materials, solvent, etc. may be recovered and the target product, 5-alkylamino-P-menthene-1, may be obtained by distillation or other methods. Next, a method for synthesizing 5-alkylamino-P-menthene-1 via a route from N-(3-methylbutylidene)-alkylamine and isoprene will be explained.
この反応経路による合成は、Ｎ−（３−メチルプチリデ
ン）ーアルキルアミンとイソプレンとが金属ナトリウム
の作用によって、一且ラバンジュラールアルドイミンの
カルバニオンを生成し環化して５ーアルキルアミノーＰ
ーメンテン−１が生成する。In the synthesis according to this reaction route, N-(3-methylbutylidene)-alkylamine and isoprene are cyclized to form a carbanion of mono-labandural aldimine by the action of sodium metal, and 5-alkylamino-P
-Menten-1 is generated.
この反応はベンゼン等の溶媒の存在下に、Ｎ−（３ーメ
チルーブチリデン）アルキルアミンに対するイソプレン
のモル比を１以上好ましくは当モル前後使用し、アルカ
リ金属も１モル以下の使用でよい。反応はベンゼン等の
溶媒の沸点以下特には４０〜５０００附近で激しい櫨洋
に行うのが好ましい。反応後は、通常の処理により触媒
の分解、未反応分の回収、蒸留等によって目的物たる５
−アルキルアミ／−Ｐ−メンテン−１を取得すればよい
。This reaction is carried out in the presence of a solvent such as benzene, using a molar ratio of isoprene to N-(3-methyl-butylidene)alkylamine of 1 or more, preferably around the same molar, and an alkali metal of 1 molar or less. . The reaction is preferably carried out at a temperature below the boiling point of a solvent such as benzene, particularly around 40 to 5,000, in a violent manner. After the reaction, the target product, 5
-alkyl amide/-P-menthene-1 may be obtained.
このように、本発明はＮ−（３ーメチルブチリデン）−
アルキルアミンを出発物質として高収率で５−アルキル
アミノーＰ−メンテンー１を得ることができる。Thus, the present invention provides N-(3-methylbutylidene)-
5-Alkylamino-P-menthene-1 can be obtained in high yield using alkylamines as starting materials.
この５−アルキルアミ、ノーＰ−メンテン−１は、アル
キルアミン基のヒドロキシル基への変換により容易にメ
ントールとすることができる。実施例 １
【１）ジヒドロラバンジュラ−ルアルドイミンの合成。This 5-alkylamine, no-P-menthen-1, can be easily converted into menthol by converting the alkylamine group into a hydroxyl group. Example 1 [1] Synthesis of dihydroravandural aldimine.
−１５ｏｏに冷却された１．０夕（１仇ｈｍｏｌ）のジ
ィソプロピルアミンを含むへキサン溶液を１５％のｎ−
ブチルリチウムヘキサン溶液４．３のこ加え１５分燈梓
後、５の‘の乾燥エーテルに溶解した新たに蒸留した１
．４夕（他ｈｍｏｌ）のＮ−（３ーメチルブチリデン）
−ｔブチルアミンを蝿梓下１５分かかって滴下した。更
に一１５ｏ０で５時間縄拝した。かくして得られた溶媒
を５泌の乾燥ェ−テルに熔解したプレニルクロラィド２
１夕（２仇ｈｍｏｌ）に加え−１５ｏｏで１時間、次い
で２０℃で２時間反応した。A hexane solution containing 1.0 hmol of diisopropylamine cooled to 15% n-
Butyl lithium hexane solution 4.3% of freshly distilled 1% dissolved in dry ether after 15 minutes of heating
．． N-(3-methylbutylidene)
-t-butylamine was added dropwise over a period of 15 minutes. Furthermore, I prayed for 5 hours at 15o0. Prenyl chloride 2 was obtained by dissolving the solvent thus obtained in 5 parts of dry ether.
The mixture was reacted for 1 night (2 hmol) at -15oo for 1 hour and then at 20°C for 2 hours.
反応生成液を砕永上に注ぎ次いでオレンジ色の油層を分
離し、水層はエーテルで２度抽出した。有機層を合せ水
洗し無水三硝で乾燥した後、溶媒及び禾反応プレニルク
ロライド及びＮ−（３ーメチルブチリデン）−ｔ−ブチ
ルアミンを回収後、１．８夕のジヒドロラバンジュラー
ルアルドィミンを蒸留分取した。（ｂ．ｐ．８１〜８４
℃／側日夕）（収率９０％、このアルドイミンはＭＡＳ
Ｓ，ＮＭＲ，ＩＲ等によって同定した。）■ ジヒドロ
ラバンジユラールアルドイミンの環化反応。The reaction product liquid was poured onto a crushed plate, and the orange oil layer was separated, and the aqueous layer was extracted twice with ether. The organic layers were combined, washed with water, and dried over anhydrous trisulfuric acid. After recovering the solvent and the reaction prenyl chloride and N-(3-methylbutylidene)-t-butylamine, dihydrorabandural aldimine of 1.8 hours was added. It was fractionated by distillation. (b.p.81-84
°C/side temperature) (90% yield, this aldimine is MAS
It was identified by S, NMR, IR, etc. )■ Cyclization reaction of dihydrolabandural aldimine.
乾燥ベンゼン１０の‘にジヒドロラバンジュラールアル
ドイミン１．０夕（８ｈｍｏｌ）及びイソプレン０．１
夕を溶解し、これに０．１夕の金属ナトリウムを加えて
５５二０で６時間処理した。1.0 mol of dihydrorabandural aldimine (8 hmol) and 0.1 mol of isoprene in 10 ml of dry benzene
The solution was dissolved and 0.1 mol of metallic sodium was added thereto, and the mixture was treated at 5,520 ml for 6 hours.
この反応生成物を５泌のエタノールと混合した後エーテ
ル抽出した。エーテル層を苧硝水溶液で洗浄後、無水若
硝で乾燥した。エーテル等を留去後、蒸留によって０．
８夕の無色の油状物を得た。（ｂ．ｐ．８２〜１００午
０／５肋日夕）この油状物はガスクロマトグラフにより
４０％のジヒドロラバンジユフールアルドイミンと５８
％の５一ｔ−ブチルアミノ−Ｐーメンテン−１を含んで
いた。実施例 ２
乾燥ベンゼン５叫に溶解した１．４夕（１皿ｍｏｌ）の
Ｎ−（３ーメチルプチリデン）−ｔーブチルアミンと１
．２夕（ｌａｈｍｏｌ）のイソプレンに０．１夕（４ｍ
ｍｏｌ）の金属ナトリウムとを耐圧反応容器中で４０ｑ
ｏ、２加持間激しく灘拝し乍ら反応させた。The reaction product was mixed with 5 volumes of ethanol and then extracted with ether. The ether layer was washed with a ramie aqueous solution, and then dried with anhydrous wakishite. After distilling off ether etc., it is distilled to 0.
8 hours of colorless oil was obtained. (b.p. 82-100 p.m. 0/5 p.m.) This oily substance was determined by gas chromatography to contain 40% dihydrolavandium furaldimine and 58%
% of t-butylamino-P-menthene-1. Example 2 1.4 liters (1 mol) of N-(3-methylbutylidene)-tert-butylamine dissolved in 50% dry benzene and 1
．． 2 mols (lahmol) of isoprene to 0.1 mols (4 m
mol) of metallic sodium in a pressure-resistant reaction vessel.
o, I reacted while worshiping violently for 2 hours.
反応後エタノールを加え、実施例１一脚と同様に後処理
した後蒸留によって１．３夕の油状物を得た（ｂ．ｐ．
４４〜７ぞＣ／１柳日夕）この油状物はガスクロマトグ
ラフによって分析の結果４％のＮ−（３ーメチルブチリ
デン）ｔーブチルアミンと８３％の５−ｔ−ブチルアミ
ンーＰーメンテン−１を含有していた。尚、実施例１，
２とも５一ｔ−ブチルアミノ−Ｐ−メンテン１であるこ
とはＮＭＲ．ＮねＳＳ．ＩＲ等で確認した。After the reaction, ethanol was added and after-treatment was carried out in the same manner as in Example 1, followed by distillation to obtain an oily substance of 1.3 days (b.p.
This oily substance was analyzed by gas chromatography and found to contain 4% N-(3-methylbutylidene)t-butylamine and 83% 5-t-butylamine-P-menthene-1. was. In addition, Example 1,
NMR. NneSS. This was confirmed through IR etc.
Claims (1)
イソプレンを溶媒中等モル以下のアルカリ金属の存在下
反応させることを特徴とする５−アルキルアミノ−Ｐ−
メンテン−１の合成法。 ２ Ｎ−（３−メチルブチリデン）−アルキルアミンと
等モル以上のプレニルクロライドをリチウムジアルキル
アミドの存在下反応させジヒドロラバンジユラ＊ルアル
ドイミンを得、次にジヒドロラバンジユラールアルドイ
ミンを溶媒中アルカリ金属の存在下反応させるとを特徴
とする５−アルキルアミノ−Ｐ−メンテン−１の合成法
。[Claims] 5-Alkylamino-P- characterized in that 1 N-(3-methylbutylidene)-alkylamine and isoprene are reacted in the presence of an alkali metal in an amount equal to or less than the same molar amount as a solvent.
Synthesis method of Menthene-1. 2 N-(3-Methylbutylidene)-alkylamine and more than the same mole of prenyl chloride are reacted in the presence of lithium dialkylamide to obtain dihydrolavandural*aldimine, and then dihydrolavanduralaldimine is reacted with an alkali in a solvent. 1. A method for synthesizing 5-alkylamino-P-menthene-1, characterized by carrying out the reaction in the presence of a metal.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11692175A JPS6039068B2 (en) | 1975-09-27 | 1975-09-27 | Synthesis method of 5-alkylamino-P-menthen-1 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11692175A JPS6039068B2 (en) | 1975-09-27 | 1975-09-27 | Synthesis method of 5-alkylamino-P-menthen-1 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5242848A JPS5242848A (en) | 1977-04-04 |
| JPS6039068B2 true JPS6039068B2 (en) | 1985-09-04 |
Family
ID=14698954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11692175A Expired JPS6039068B2 (en) | 1975-09-27 | 1975-09-27 | Synthesis method of 5-alkylamino-P-menthen-1 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6039068B2 (en) |
-
1975
- 1975-09-27 JP JP11692175A patent/JPS6039068B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5242848A (en) | 1977-04-04 |
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