Acetic Acid → 4-(1-Methylpiperidin-4-yl)benzamide

Participants

Reaction Steps

To a solution of 4-piperidin-4-ylbenzamide (200 mg, 1.00 mmol), 37% aqueous formaldehyde (162 μL, 2.00 mmol), and acetic acid (86 uL, 1.5 mmol) in a mixture of dichloromethane and methanol (2:1, 6 mL) was added sodium triacetoxylborohydride (318 mg, 1.5 mmol) in portions over fifteen minutes and stirring was continued for 2 hr at room temperature. The reaction was then quenched with water and adjusted to pH 9 with 2N aqueous sodium hydroxide then extracted with dichloromethane (2×50 ml). The organic extracts were combined and dried over sodium sulfate, filtered and concentrated to give 4-(1-methylpiperidin-4-yl)benzamide (190 mg, 87%). MS (EI) for C13H18N2O: 218 (MH+).

Provenance & Evidence