Hydrochloric Acid → 1-[4-(Methylsulfonyl)phenyl]-4-(1-pyrrolidinyl)piperidine

Participants

Reaction Steps

A solution of 2 g (0.0065 mol) of the compound of (C), 5 ml of 4.66M HCl (in isopropyl alcohol), 40 ml of methylene chloride and 2.68 g of tetrabutylammonium cyanoborohydride is stirred at ambient temperature overnight. The solution is diluted with sat. Na2CO3 solution and extracted with methylene chloride. The combined extracts are dried (Na2SO4) and concentrated in vacuo to give 1.6 g (80%) of the title compound. An analytical sample is prepared by recrystallization from ethyl acetate: m.p. 166°-170° C.; IR (KBr) 1595, 1295, and 880 cm-1 ; NMR (CDCl3)δ7.75 (d, 2H); 6.9 (d, 2H), 4.0-3.7 (m, 1H), 3.15-2.55 (m, 8H), 3.0 (s, 3H), and 2.05-1.55 (m, 8H)

Provenance & Evidence