Hydrochloric Acid → HCID 66938556, compound

Participants

Reaction Steps

Combine 1-methyl-4-(N-(3-nitro-5-fluorophenyl)methylamino)piperidine (Preparation 28) (0.06 g, 0.22 mmol), iron dust (0.06 g, 1.12 mmol), methanol (5 mL) and 1M HCl (0.22 mL, 0.22 mmol), stir, and heat at reflux for 18 hr. Cool the reaction mixture to ambient temperature, dilute with ethyl acetate (50 mL), and add 1N sodium hydroxide solution until basic (pH=9). Separate organic layer, wash with saturated aqueous NaCl solution, dry over sodium sulfate, filter, and concentrate to obtain 0.036 g (69%) of the title intermediate: 1H NMR (CDCl3): 5.9 (m, 1H), 5.7 (m, 2H), 3.6 (bs, 2H), 3.4 (m, 1H), 2.9 (m, 2H), 2.7 (s, 3H), 2.3 (s, 3H), 2.0 (m, 2H), 1.8 (m, 2H), 1.7 (m, 2H).

Provenance & Evidence