Process for preparing N-(5-chloro-2-isopropylbenzyl)cyclopropanamine

A technology of isopropyl and cumene, applied in the field of preparing N-cyclopropylamine, can solve the problem of high production cost

Inactive Publication Date: 2017-08-18
BAYER CROPSCIENCE AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Furthermore, in WO 2009 / 055674 the desired compound was isolated in only 18% yield
Both of these methods make it very expensive to generate

Method used

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  • Process for preparing N-(5-chloro-2-isopropylbenzyl)cyclopropanamine
  • Process for preparing N-(5-chloro-2-isopropylbenzyl)cyclopropanamine
  • Process for preparing N-(5-chloro-2-isopropylbenzyl)cyclopropanamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0206] Embodiment 1: 2-bromo-1-isopropyl-4-nitrobenzene of general formula (XI)

[0207] 1,3-Dibromo-5,5-dimethylhydantoin (86.9 g, 0.298 mol) was added to p-nitrocumene (X) (100 g , 0.581mol, GC purity 96%) and sulfuric acid (178g, 1.743mol, 98% strength) solution. The mixture was then warmed to room temperature and stirred for an additional 1 hour. The reaction mixture was poured onto 200 g of ice water and mixed with sodium disulfide (15.1 g, 0.06 mol) and toluene (300 g). The phases are then separated. The organic phase was washed with 5% strength aqueous sodium hydroxide solution and the toluene was distilled off under reduced pressure. 2-Bromo-1-isopropyl-4-nitrobenzene was obtained as a pale yellow oil (147 g, 93.6 GC-%, based on area, 97% of theory).

[0208] A solution of p-nitrocumene (X) (50 g, 0.300 mol, GC purity: 99.1%) and iron (III) chloride was heated to 40° C. and bromine (59.92 g, 0.375 mol) was added dropwise within 3 hours. The reaction was poured i...

Embodiment 2

[0211] Embodiment 2: 3-bromo-4-isopropylaniline of general formula (VII)

[0212] A solution of sodium sulfide (31.2 g, 0.24 mol) and sulfur (7.7 g, 0.24 mol) was stirred at 80° C. for 15 minutes. Isopropanol (160 g) was then heated and the mixture was stirred at 75° C. for another 15 minutes, and finally 2-bromo-1-isopropyl-4-nitrobenzene (XI) (50 g, 0.19 mol ). After stirring for an additional 5 hours, the reaction was complete. For work-up, the isopropanol was first distilled off and the remaining mixture was extracted with toluene / chlorobenzene. The combined organic phases were distilled off under reduced pressure. 3-Bromo-4-isopropylaniline was obtained as a red oil (42 g, 91 GC-%, based on area, 93% of theory).

[0213] 2-Bromo-1-isopropyl-4-nitrobenzene (XI) (20 g, 79.1 mmol, 96.5 GC%, based on area), methanol (400 ml), platinum on carbon (1% platinum, 2 % of alum, wet with water) (1.0g, 0.018 mmol) and zinc dibromide (90 mg, 0.40 mmol) were placed in a 600ml aut...

Embodiment 3

[0221] Embodiment 3: 2-bromo-4-chloro-1-cumene of general formula (IV)

[0222] Hydrochloric acid (152 g, 31% strength, 1.29 mol) was added dropwise to a suspension of 3-bromo-4-isopropylaniline (VII) (100 g, 0.43 mol) and water (150 g) at room temperature. The suspension was then cooled to 5°C and a solution of sodium nitrite (32.7 g, 0.46 mol) in water (140 g) was added dropwise within 2 hours. After stirring for a further 1 hour, sulfamic acid (2.5 g, 0.026 mol) was added. Copper (I) chloride (10.8 g, 0.11 mol), hydrochloric acid (202 g, 31%, 1.72 mol) and water (75 g) were added to a second flask, and the previously formed diazonium salt was added dropwise over 30 minutes . After stirring for a further 1.5 hours, the mixture was extracted with dichloromethane (250 g), the phases were separated and the dichloromethane was distilled off under reduced pressure. The obtained crude product was purified by distillation. 2-Bromo-4-chloro-1-isopropylbenzene was obtained as a...

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Abstract

The present invention relates to a process for preparing N-(5-chloro-2-isopropylbenzyl)cyclopropanamine by hydrogenation of N-[(5-chloro-2-isopropylphenyl)methylene]cyclopropanamine over specific platinum catalysts.

Description

[0001] This application is a divisional application of the 201380021718.2 invention patent application entitled "Method for preparing N-(5-chloro-2-isopropylbenzyl)-cyclopropylamine" submitted on April 25, 2013. technical field [0002] The present invention relates to a process for the preparation of N-(5-chloro-2-isopropyl) by hydrogenation of N-[(5-chloro-2-isopropylphenyl)methylene]cyclopropylamine under a specific platinum catalyst benzyl)-cyclopropylamine method. Background technique [0003] Processes for the bromination of strongly deactivated aromatic compounds, such as p-alkyl-substituted nitrobenzenes or nitrobenzenes themselves, are described in the literature. Bromination of p-nitroethylbenzene by iron and bromine has been published in very low yields (55% crude, 34% after distillation) and requires long reaction times of more than 24 hours (J.Am. Chem. Soc. 1950, 72, 2804). The yield of bromination of nitrobenzene using iron and bromine has been 60-75% of the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/26C07C211/40
CPCC07C17/2632C07C45/45C07C209/26C07C249/02C07C211/40C07C251/24C07C47/55C07C25/06C07F3/02C07C2601/02Y10S585/931C07C211/37C07C17/093C07C45/004C07C201/12C07C209/00C07C209/365C07C209/70C07C245/20C07C251/04C07C209/52C07C205/06C07C209/68C07C211/52C07C25/02
Inventor T·希姆莱S·莱曼T·N·穆勒M·瑞里奇L·罗德菲尔德F·福尔兹S·冯 摩根斯特恩
Owner BAYER CROPSCIENCE AG
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