Water → HCID 21413266, compound

Participants

Reaction Steps

A solution of 1-[2-(o-nitrophenyl)ethyl]-4-benzamidopiperidine (4.25 g.) in absolute ethanol (150 ml.) was added over 50 minutes to stirred stannous chloride (10.82 g.) in concentrated hydrochloric acid (12 ml.).and water (7.5 ml.) at 60°-70° C. After addition, the mixture was stirred at this temperature for 4 hours before cooling and evaporating the ethanol. Continuous extraction into chloroform of the neutralised (with 2 N sodium hydroxide solution) aqueous fraction gave the title compound (1.65 g.). The aqueous layer after extraction was made alkaline with 2 N sodium hydroxide solution and extracted with more chloroform to give a further batch of the title compound (2.36 g.). The total product was crystallised from ethanolic hydrogen chloride and ether to give the hydrochloride of the title compound (2.75 g.), m.p. 263.8° C. (Found: C, 60.3; H, 7.0; N, 10.5. C20H25N3O. 2HCl requires C, 60.6; H, 6.9; N, 10.60%).

Provenance & Evidence