Hydrochloric Acid → HCID 18617570, compound

Participants

Reaction Steps

A mixture of 4-(4-oxo-piperidin-1-yl)-benzonitrile (100 mg, 0.5 mmol, reference example 116) dimethylamine hydrochloride (408 mg, 5 mmol) and NaCNBH3 (25 mg, 0.4 mmol) was dissolved in MeOH (7 mL) and stirred at room temperature overnight. After 24 h, additional NaCNBH3 (24 mg, 0.38 mmol) was added and the mixture was stirred overnight at room temperature. The pH of the mixture was adjusted to pH 2 with concentrated HCl and extracted with Et2O (3×). The aqueous phase was adjusted to pH 10 with KOH pellets, and extracted (3×) with Et2O. The latter combined organic phases were washed with brine, dried with Na2SO4, filtered and evaporated. The crude material was taken into the next step without further purification. 1H NMR (CDCl3): δ 7.44 (d, 2H), 6.83 (d, 2H), 3.86 (m, 2H), 2.86 (dt, 2H), 2.32-2.38 (m, 1H), 2.28 (s, 6H), 1.92 m(m, 2H), 1.54 (dq, 2H). MS (EI) m/z 229 (M+H)+.

Provenance & Evidence