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

HRID 2064077Notes

Reaction equation

[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:25]([O-])=O)=[C:9]([NH:11][CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)[CH:10]=1)[CH3:3].O.NN>C(O)C.[Ni]>[NH2:25][C:8]1[CH:7]=[CH:6][C:5]([O:4][CH:2]([CH3:1])[CH3:3])=[CH:10][C:9]=1[NH:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[CH2:14][CH2:13]1

Participants

Conditions

Temperature: 45 °C

Procedure

A partial solution of 1,1-dimethylethyl 4-({5-[(1-methylethyl)oxy]-2-nitrophenyl}amino)-1-piperidinecarboxylate (D47, 514 mg, 1.35 mmol) in ethanol (20 ml) was treated with Raney Nickel followed by dropwise addition of a solution of hydrazine hydrate (0675 ml, 13.5 mmol) in ethanol. The mixture was heated at 45° C. for 2 hrs, then the Raney Nickel was filtered off washing with ethanol and the filtrate concentrated under vacuum to afford the title compound as a violet coloured oil (470 mg, 99%).

Workup

filtrationthe Raney Nickel was filtered off
washwashing with ethanol
concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record: ord-c0a8713650cd4b9096ed018de8d2de15
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288413B2

Reaction notes

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