Acetaldehyde → HCID 66938866, compound

Participants

Reaction Conditions

Reaction Steps

Add acetaldehyde (0.817 g) to a solution of 1-methyl-4-(3-chloro-2-fluorophenylamino)piperidine (Preparation 19) (0.45 g), sodium cyanoborohydride (0.123 g) and trifluoroacetic acid (0.633 g) in methanol (20 mL) and heat in a sealed tube at 80° C. for three days. Load on a SCX column (10 g), wash with methanol, elute with 2M NH3 in methanol, evaporate, and further purify on a silica gel column (35 g), using a gradient of dichloromethane-2M NH3 in methanol to give 0.50 g of the title intermediate as a colorless oil: mass spectrum (electric spray) m/z=271 (+1); 1H NMR (CDCl3): 6.94 (m, 3H), 3.14 (q, J=7.0 Hz, 2H), 3.06 (m, 1H), 2.84 (br d, 2H), 2.22 (s, 3H), 1.93 (m, 2H), 1.74 (m, 4H), 0.95 (t, J=7.0 Hz, 3H).

Provenance & Evidence