Hydrazine hydrate (1:1) → 1,1-Dimethylethyl 4-[(2-amino-5-chloro-4-methylphenyl)amino]-1-piperidinecarboxylate

Participants

Reaction Conditions

Reaction Steps

1,1-Dimethylethyl 4-[(5-chloro-4-methyl-2-nitrophenyl)amino]-1-piperidinecarboxylate (D6) (0.270 mmol, 100 mg) was dissolved in ethanol (10 ml) and an aqueous suspension of Raney-Nickel (0.3 ml) was added at room temperature; the mixture was heated to 40-50° C. and hydrazine monohydrate (15 eq., 4 mmol, 0.14 ml) was added over 20-30 min; the reaction mixture was then heated at 40° C. for 10 extra minutes and then it was then cooled to room temperature, filtered through celite and the solvent was evaporated to yield the crude product. Crude product was subsequently purified by chromatography (ethyl acetate/hexane) to yield the title compound, 80 mg, 88%, M+−Boc=240.

Provenance & Evidence