HCID 9797645, compound → HCID 9819036, compound

Participants

Reaction Steps

A mixture of 2-(4-[3-phenylpropyl]-1,2,3,6-tetrahydropyridin-1-ylmethyl)benzimidazole (1.01 g, 3.05 mmol) and platinum (IV) oxide hydrate (56 mg) in ethyl acetate (75 ml) was hydrogenated on a Parr apparatus (30 psi maximum) for 70 minutes. Fresh catalyst was added (40 mg) and the mixture hydrogenated for a further 2.5 h. The mixture was filtered and evaporated to dryness. Flash chromatography eluting with 7.5% methanol in dichloromethane followed by recrystallisation from ethyl acetate/petrol (60°-80° C.) gave the title compound (0.52 g, 52%) as a white solid, m.p. 140°-141° C.; (Found: C, 79.25; H, 8.07; N, 12.39. C22H27N3 requires C, 79.24; H, 8.16; N, 12.60%); δH (DMSO-d6) 1.19 (SH, m, 2×CH2 +piperidinyl CH), 1.57 (4H, m, 2×CH2), 2.02 (2H, m, CH2), 2.55 (2H, m, piperidinyl CH2), 2.81 (2H, m, piperidinyl CH2), 3.66 (2H, s, CH2N), 7.15 (SH, m, ArH), 7.26 (2H, m, ArH), 7.43 (1H, br d, ArH), 7.51 (1H, br d, ArH), and 12.16 (1H, br s, N3H); m/z (CI+, NH3) 334 (M+1)+.

Provenance & Evidence