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

HRID 2064139Notes

Reaction equation

[F:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH:9][CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[C:4]([N+:23]([O-])=O)[CH:3]=1.O.NN>C(O)C.[Ni]>[NH2:23][C:4]1[CH:3]=[C:2]([F:1])[C:7]([CH3:8])=[CH:6][C:5]=1[NH:9][CH:10]1[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15]1

Participants

Conditions

Temperature: 45 °C

Procedure

1,1-Dimethylethyl 4-[(4-fluoro-5-methyl-2-nitrophenyl)amino]-1-piperidinecarboxylate (D27) (0.96 mmol, 340 mg) in ethanol (20 mL) was treated under argon at room temperature with Raney Nickel (suspension, 50% in water, 0.5 mL) then dropwise with hydrazine hydrate (9.6 mmol, 10 eq) in ethanol over 15 min. The mixture was heated at 45° C. for 50 min. The Raney nickel was filtered off and washed with ethanol. The reaction mixture was concentrated under vacuum to give the title compound (0.88 mmol, 284 mg, 92% yield). M+H=324.16.

Workup

filtrationThe Raney nickel was filtered off
washwashed with ethanol
concentrationThe reaction mixture was concentrated under vacuum

Sources & evidence

ORD record: ord-824004b3439b4d94975c2c8858a6c710
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288412B2

Reaction notes

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