Synthesis
The general procedure for the synthesis of 5-nitro-2-piperidinebenzonitrile from hexahydropyridine and 2-chloro-5-nitrobenzonitrile was as follows: a mixture of 2-chloro-5-nitrobenzonitrile (2 g, 10.96 mmol, 1 eq.), potassium carbonate (4.54 g, 32.7001 mmol, 3 eq.), piperidine (1.63 mL, 16.34 mmol, 1.5 eq.) and DMF ( 5 mL) mixture was stirred at 90°C for 3 hours until the reaction was complete. After the reaction was complete, the oil bath was removed. The reaction mixture was diluted with 100 mL of ethyl acetate (EA) and washed sequentially with saturated ammonium chloride solution and saturated sodium chloride solution. The aqueous phase was then extracted with ethyl acetate. All organic phases were combined and dried with anhydrous sodium sulfate. After filtration, the filtrate was concentrated to give the yellow solid product 5-nitro-2-piperidine benzonitrile (2.528 g, 99% yield).
References
[1] Patent: CN106892871, 2017, A. Location in patent: Paragraph 0135-0137
[2] Patent: US2003/203909, 2003, A1
[3] European Journal of Organic Chemistry, 2007, # 8, p. 1378 - 1383
[4] Patent: EP1176140, 2002, A1. Location in patent: Page 53
