Acetic Acid → HCID 58997344, compound

Participants

Reaction Steps

Combine (3-(1-methylpiperidin-4-ylamino)phenyl)carbamic acid tert-butyl ester (Preparation 9, 1.15 g, 3.77 mmol), methanol (15 mL) and formaldehyde (37% aq., 0.92 mL, 11.3 mmol). Stir at room temperature for 45 min. Cool to 0° C. Add acetic acid (0.22 mL, 3.77 mmol) and sodium cyanoborohydride (414 mg, 6.59 mmol). Stir at room temperature overnight. Concentrate to dryness. Dissolve the residue in a 2/1 mixture of ethyl acetate and hexanes (20 mL) and wash with sodium hydroxide (1N aq., 2×20 mL). Separate the organic layer and dry over magnesium sulfate. Filter and concentrate under reduced pressure. Purify through flash chromatography eluting with a 20/1 mixture of dichloromethane and 2M ammonia in methanol to provide the title compound (990 mg, 82%): mass spectrum (ion spray): m/z=320.3 (M+1).

Provenance & Evidence