Synthetic method of 2-(7-methoxyl-1-naphthyl) ethylamine hydrochloride

A technology of ethylamine hydrochloride and methoxy group is applied in the field of synthesis of 2-(7-methoxy-1-naphthyl)ethylamine hydrochloride, which can solve problems such as being difficult to realize industrialized production, and achieve the steps of Concise, high reaction yield, beneficial to the effect of industrialization promotion

Inactive Publication Date: 2013-05-22
SHANDONG FANGMING PHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When this method prepares 2-(7-methoxy-1-naphthyl)ethylamine, the hydrogenation reduction pressure is as high as 300 atmospheres, and it is difficult to realize industrial production

Method used

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  • Synthetic method of 2-(7-methoxyl-1-naphthyl) ethylamine hydrochloride
  • Synthetic method of 2-(7-methoxyl-1-naphthyl) ethylamine hydrochloride
  • Synthetic method of 2-(7-methoxyl-1-naphthyl) ethylamine hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1: Synthesis of (7-methoxy-3,4-dihydro-1-naphthyl)acetonitrile

[0034] At room temperature, successively put 176 g of 7-methoxytetralin-1-one, 128 g of cyanoacetic acid, 1600 ml of toluene, 27 g of benzylamine, and 33 g of heptanoic acid into a 2L reaction flask, start stirring, and heat for 114 Reflux at ℃ to separate water for about 16 hours. After all the substrates have reacted, stop heating. After cooling down to room temperature naturally, cool down in an ice-water bath to below 10℃ to precipitate a pale yellow solid. Filter and wash the filter cake with toluene. Wash the filtrate with 500ml, 2mol / L sodium hydroxide solution, separate the toluene phase, wash the toluene phase with 500ml purified water again, separate the liquids, and finally wash the toluene phase with 500ml saturated saline, separate the liquids, and put the toluene phase at 70- Concentrate to dryness under reduced pressure at 75°C, and the remaining brown oil is directly used in th...

Embodiment 2

[0035] Embodiment 2: the synthesis of (7-methoxy-1-naphthyl) acetonitrile

[0036] At room temperature, dissolve 100 g of (7-methoxy-3,4-dihydro-1-naphthyl)acetonitrile in 500 ml of dichloromethane, and the solution turns reddish brown. Add 125 g of DDQ and 1000ml of dichloromethane into a 2L reaction flask in turn, start stirring, heating, and add the dichloromethane solution of intermediate I dropwise at a controlled temperature of 25-28°C, and keep warm at 30±2°C for 1 hour after dropping. After heat preservation, filter, and wash the filtrate 3 times with 500ml saturated sodium bicarbonate solution, separate the dichloromethane layer, wash with 500ml water again, and separate the layers; finally wash the dichloromethane phase with 500ml saturated saline, and separate the layers. The dichloromethane phase was concentrated to dryness under reduced pressure at 30-35°C, and the remaining yellow oil was dissolved by adding 260ml of ethanol, cooled in an ice-water bath to cool...

Embodiment 3

[0037] Example 3: Synthesis of 2-(7-methoxy-1-naphthyl)ethylamine hydrochloride

[0038] At room temperature, dissolve 80 g of (7-methoxy-1-naphthyl)acetonitrile in 800 ml of anhydrous tetrahydrofuran, add 90 g of calcium chloride, control the temperature at 0-5°C, and add 31 g of sodium borohydride in batches , After the addition, rise to room temperature and react for 5h. After the reaction was completed and filtered, the filtrate was concentrated to dryness under reduced pressure at 50°C, and the remaining yellow oil was dissolved by adding 320ml of ethyl acetate, filtered hot, and about 30ml of hydrochloric acid was added to adjust the pH to 2-3, cooling and crystallization, stirring at 10°C for 1 -2h, filter, and dry the filter cake at 50°C to obtain 2-(7-methoxy-1-naphthyl)ethylamine hydrochloride.

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Abstract

The invention relates to a synthetic method of 2-(7-methoxyl-1-naphthyl) ethylamine hydrochloride. The method comprises the following steps of: reacting 7-methoxyl-1-naphthyl (a compound IV) with cyanoacetic acid to prepare (7-methoxyl-3,4-dihydro-1-naphthyl) acetonitrile (a compound III); performing deep drawing quality (DDQ) dehydrogenation to prepare (7-methoxyl-1-naphthyl) acetonitrile; using sodium borohydride as a reducing agent and reacting sodium borohydride with calcium chloride in anhydrous tetrahydrofuran to react to obtain 2-(7-methoxyl-1-naphthyl) ethylamine; and satisfying with hydrochloric acid to obtain a compound I, wherein the compound is an important intermediate of synthetic agomelatine.

Description

technical field [0001] The invention relates to a synthesis method of 2-(7-methoxy-1-naphthyl)ethylamine hydrochloride, belonging to the technical field of drug synthesis. Background technique [0002] Depression (DEP) is a common mood disorder in psychiatry, with significant and persistent low mood as the main clinical feature, and the low mood is not commensurate with the situation. Clinically, it mainly includes: depression (severe depression), dysthymia, depression associated with brain or physical diseases, depression associated with mental disorders caused by psychoactive substances or non-addictive substances, and post-schizophrenia depression. Its clinical manifestations are depression, slow thinking, decreased speech and movement, and loss of interest in work. At least 10% of patients with depression may have manic episodes at different times in the future, and a diagnosis of bipolar disorder should be made at this time. Depression has become a major global mental...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/60C07C213/02
Inventor 段义杰范兴山王飞龙余洪智
Owner SHANDONG FANGMING PHARMACEUTICAL CO LTD
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