Potassium Carbonate → 2-(4-[2-Phenylethyl]piperidin-1-ylmethyl)benzimidazole

Participants

Reaction Steps

2-(Chloromethyl)benzimidazole (448 mg, 2.64 mmol) and potassium carbonate (729 mg, 5.28 mmol) were added to a solution of 4-(2-phenylethyl)piperidine (500 mg, 2.64 mmol) in dry DMF (20 ml) under a nitrogen atmosphere and the mixture stirred at room temperature for 20 hours. The reaction was diluted with water (200 ml) and extracted with ethyl acetate (3×100 ml), the combined organic layers were washed with water (25 ml) and brine (50 ml), dried (MgSO4) and evaporated in vacuo to give a brown oil which was triturated with toluene and recrystallised from methanol to give the title compound as a sandy solid (97.3 mg, 12%), m.p. 170° C.; (Found: C, 78.38; H, 7.79; N, 12.93. C21H25N3.0.1 H2O requires C, 78.51; H, 7.91; N, 13.08%); δH (DMSO-d6) 1.22 (3H, m, piperidinyl H and CH2CH2Ph), 1.50 (2H, m, piperidinyl CH2), 1.67 (2H, m, piperidinyl CH2), 2.01 (2H, m, piperidinyl CH2), 2.56-2.60 (2H, m, piperidinyl CH2), 2.83 (2H, d, J 10.8Hz, CH2 -Ph), 3.67 (2H, s, N-CH2Ar), 7.12-7.19 (5H, m, ArH), 7.24-7.28 (2H, m, ArH), 7.42 (1H, d, J 7.3 Hz, ArH), 7.53 (1H, d, 3 7.3Hz, ArH), and 12.20 (1H, brs, NH); m/z (CI+, NH3) 320 (M+1)+.

Provenance & Evidence