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

HRID 2064179Notes

Reaction equation

[CH3:1][C:2]1[C:3]([O:25][CH:26]([CH3:28])[CH3:27])=[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]([O:25][CH:26]([CH3:27])[CH3:28])[C:2]([CH3:1])=[CH:7][C:6]=1[NH:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])[CH2:11][CH2:10]1

Participants

Conditions

Temperature: 45 °C

Procedure

A suspension/solution of 1,1-dimethylethyl 4-({5-methyl-4-[(1-methylethyl)oxy]-2-nitrophenyl}amino)-1-piperidinecarboxylate (D74) (0.2 mmol, 80 mg) in ethanol (10 mL) was treated with Raney Nickel, then hydrazine hydrate (2 mmol, 100 mg, 10 eq) was added dropwise over 5 min under argon at room temperature. The mixture was then heated at 45° C. for 30 min. The catalyst was then filtered off and washed with ethanol and methanol. The filtrate was concentrated under reduced pressure to give the title compound as a solid (0.16 mmol, 60 mg, 83% yield). M+H 364.3, 308.2, 264.2 (full molecule and fragments for loss of tert-butyl group and loss of Boc group).

Workup

filtrationThe catalyst was then filtered off
washwashed with ethanol and methanol
concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-f601c347bf444e4a82ceea9f2f764892
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288412B2

Reaction notes

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