C-(2-Phenyl-Cyclohexyl)-Methylamine Compounds for the Treatment of Anxiety Disorders
a technology of methylamine and methylamine, which is applied in the direction of biocide, plant growth regulator, animal husbandry, etc., can solve the problems of inducing deep-seated despair in virtually anyone, monoamine reuptake inhibitors, and standard medications that often intensify or induce anxiety states
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Benefits of technology
Problems solved by technology
Method used
Image
Examples
example 1
Preparation of (1R,2R)-[2-(3-methoxyphenyl)-cyclohexylmethyl]-methylamine hydrochloride
[0057][2-(3-Methoxyphenyl)-cyclohexylmethyl]-methylamine and (1R,2R)-[2-(3-methoxyphenyl)-cyclohexylmethyl]-methylamine, in particular the hydrochloride salt thereof, are prepared as follows:
[0058]3.16 ml (25.2 mmol) phenyl chloroformate were added dropwise to a solution of 5.67 g (22.9 mmol) (1R,2R)-[2-(3-methoxyphenyl)-cyclohexylmethyl]-dimethylamine in 390 ml dry toluene at the boiling point. After the mixture had been heated under reflux for three hours, it was cooled to 20° C., and washed successively with 100 ml each of sodium hydroxide solution (2.5N), distilled water, hydrochloric acid (1N) and a saturated sodium chloride solution. It was dried over sodium sulfate and evaporated in vacuo. The residue was taken up in 192.5 ml ethylene glycol and 46 ml sodium hydroxide solution (5N) and the mixture was stirred at 110° C. for a total of 8 hours, it being topped up twice with 10 ml sodium hydr...
example 2
Preparation of (1R,2R)-3-(2-methylaminomethyl-cyclohexyl)-phenol hydrochloride
[0059]3.55 g (15.2 mmol) of the product from example 1 were stirred under reflux in 4.59 ml hydrobromic acid (47-48% HBr) for 7.5 h. After cooling, ice / water was added and the mixture was then rendered alkaline with sodium hydroxide solution (6N). It was extracted three times with 50 ml ethyl acetate each time. The extracts were washed with a saturated sodium chloride solution, dried over sodium sulfate and evaporated in vacuo. The residue (2.91 g) was dissolved in 16.4 ml 2-butanone and converted into the hydrochloride with 1.63 ml trimethylchlorosilane as described under example 1. By this procedure, 2.98 g (76.5% of theory) of the title compound were obtained as a slightly yellow-colored solid which melted at 173-175° C.
example 3
Preparation of sulfuric acid mono-(1R,2R)-[3-(2-dimethylaminomethyl-cyclohexyl)-phenyl]ester
[0060]Sulfuric acid mono-[3-(2-dimethylaminomethyl-cyclohexyl)-phenyl]ester or sulfuric acid mono-(1R,2R)-[3-(2-dimethylaminomethyl-cyclohexyl)-phenyl]ester was prepared as follows:
[0061]15.9 g (4.70 mmol) of a 2.9% strength solution of sulfuric acid in dimethylformamide were added dropwise to a solution of 1.00 g (3.92 mmol) (1R,2R)-3-(2-dimethylaminomethyl-cyclohexyl)-phenol; hydrochloride and 0.94 g (4.70 mmol) dicyclohexylcarbodiimide in 20 ml dimethylformamide at 0° C., while stirring. When the addition had ended, the mixture was stirred further for another 10 minutes and a pH of 9 was then established with dilute ammonium hydroxide solution. The precipitate formed was separated off, washed with ethyl acetate and dried in vacuo. 0.26 g (21% of theory) of the title compound was obtained in this way as a white solid.
PUM
Login to View More Abstract
Description
Claims
Application Information
Login to View More