Ammonium Hydroxide → 4-Piperidinecarboxamide

Temperature

70 °C

4-(4-chloro-phenyl-amino)-1-phenylmethyl)-4-piperidine-carbonitrile (29.3 g) was dissolved in 150 ml conc. sulfuric acid and stirred for 1 h at room temperature and 1 h at 70° C. Then the reaction mixture was cooled to room temperature and poured on ice, adjusted to pH 10 by addition of 30% aqueous ammonium hydroxide and extracted three times with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered and evaporated to yield 4-(4-chloro-phenyl-amino)-1-phenylmethyl)-4-piperidine-carboxamide as an brownish oil which crystallized upon addition of 50 ml diethyl ether and 50 ml pentane. Off-white powder (11.84 g), m.p. 167-170° C.

1. temperatureThen the reaction mixture was cooled to room temperature
2. additionpoured on ice
3. extractionextracted three times with dichloromethane
4. dry with materialThe combined organic layers were dried over sodium sulfate
5. filtrationfiltered
6. customevaporated

ORD record

ord-21467c482ced4dea8741f76f5b5dafbf

Source dataset

uspto-grants-2000_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06043366