Ammonia → HCID 59204976, compound

Participants

Reaction Steps

A mixture of 1-(2-fluoro-4-nitrophenyl)piperidin-4-one (compound of Reference Example 26; 5.00 g, 2.10 mmol), methylamine hydrochloride (2.83 g, 4.20 mmol), titanium tetraisopropoxide (11.9 g, 4.20 mmol), triethylamine (4.25 g, 4.20 mmol) and ethanol (25 ml) was stirred at room temperature for 16 hours under argon atmosphere. Sodium borohydride (1.58 g, 4.20 mmol) was added to the reaction mixture, and the mixture was stirred at room temperature for 7 hours. 2.8N aqueous ammonia (25 ml) was added to the reaction mixture at 0° C., and the mixture was stirred for 30 minutes. The reaction mixture was filtered, and the filtrate was extracted with dichloromethane. 2N aqueous hydrochloric acid was added to the organic layer, and the mixture was stirred. The water layer was adjusted to pH=12 by addition of 2N aqueous sodium hydroxide and extracted with dichloromethane. The organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (2.12 g, 40%) as a yellow-brown liquid.

Provenance & Evidence