Hydrazine hydrate (1:1) → 1,1-Dimethylethyl 4-{[2-amino-5-methyl-4-(trifluoromethyl)phenyl]amino}-1-piperidinecarboxylate

HRID 2064162Notes

Reaction equation

[CH3:1][C:2]1[C:3]([C:25]([F:28])([F:27])[F:26])=[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]([C:25]([F:28])([F:27])[F:26])[C:2]([CH3:1])=[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-methyl-2-nitro-4-(trifluoromethyl)phenyl]amino}-1-piperidine-carboxylate (D57) (3.17 mmol, 1.29 g) was dissolved in ethanol (20 ml) and an aqueous suspension of Raney-Nickel (3 ml) was added at room temperature; the mixture was heated to 40-50° C. and hydrazine monohydrate (15 eq., 48 mmol, 1.5 ml) was added over 20-30 min. The reaction mixture was then cooled to room temperature, filtered through celite and the solvent was evaporated to yield the title compound, 1.1 g, 92%, M+-Boc+H=274.

Workup

additionwas added at room temperature
temperatureThe reaction mixture was then cooled to room temperature
filtrationfiltered through celite
customthe solvent was evaporated

Sources & evidence

ORD record: ord-52eb506e10b249a3ad9582b6b7b067c9
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288412B2

Reaction notes

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