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

HRID 2064125Notes

Reaction equation

[Cl:1][C:2]1[C:3]([CH3:25])=[CH:4][C:5]([N+:22]([O-])=O)=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH:7]=1.O.NN>C(O)C.[Ni]>[NH2:22][C:5]1[CH:4]=[C:3]([CH3:25])[C:2]([Cl:1])=[CH:7][C:6]=1[NH:8][CH:9]1[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]1

Participants

Conditions

Temperature: 45 °C

Procedure

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.

Workup

additionwas added at room temperature
temperaturethe reaction mixture was then heated at 40° C. for 10 extra minutes
temperatureit was then cooled to room temperature
filtrationfiltered through celite
customthe solvent was evaporated
customto yield the crude product
customCrude product was subsequently purified by chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-ca464dabaa5944f2a16464a9827e35ea
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288412B2

Reaction notes

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