N-Acyl cyclic amine derivatives

Tsuchiya etal, US Patent 6,140,333 (October 31, 2000) Assignee Banyu Pharmaceutical Co., Ltd. 

Utility Treatment of Respiratory, Urinary and Digestive Diseases 

1-hydroxybenzotriazole, 1 -ethyl-3-(3-dimethylaminopropyl)carbodiimide vi- Methyl alocohol, hydrochloric acid 

To 4-amino-1-benzylpiperidine (25 g) dissolved in 150 ml chloroform was added di-t-butyl dicarbonate (31.4 g) with ice cooling followed by stirring 2 hours at ambient temperature. The reaction mixture was diluted with chloroform, washed with water, dried, and concentrated. After recrystallizing from hexane/diisopropyl ether, 35.65 g of product was isolated. 

The product from Step 1 (59.0 g) was dissolved in 550 ml methyl alcohol containing 24 ml HO Ac and 10% palladium-carbon (5g) and hydrogenated. Thereafter, the mixture was filtered, concentrated, diluted with chloroform, washed with NaHC03, brine, and dried. The solvent was distilled off and 53.7 g product isolated. 

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Tsuchiya, Y., Nomoto, T., Ohsawa, H., Kawakami, K., Ohwaki, K., Nishikibe, M. (Banyu Pharmaceutical Co ) Preparation of N-acyl cyclic amine derivatives as selective antagonists of muscarine M3 receptor, W09940070 (1999). 

Dainippon Sumitomo Pharma Co Ltd (2011) N-Acyl cyclic amine derivatives or pharmaceuti-caUy acceptable salt thereof. Patent WO2011/111875 (Al), US2012/214790 (Al)... 

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