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

HRID 2064189Notes

Reaction equation

HRID 2064189 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:6][C:5]([NH:12][CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)=[C:4]([N+:26]([O-])=O)[CH:3]=1.O.NN>C(O)C.[Ni]>[NH2:26][C:4]1[CH:3]=[C:2]([Cl:1])[C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:6][C:5]=1[NH:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH2:15][CH2:14]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 598501521,1-Dimethylethyl 4-({4-chloro-5-[(1-methylethyl)oxy]-2-nitrophenyl}amino)-1-piperidinecarboxylate

Product 1

HCID 598501671,1-Dimethylethyl 4-({2-amino-4-chloro-5-[(1-methylethyl)oxy]phenyl}amino)-1-piperidinecarboxylateYield 83%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Conditions

Temperature
45 °C

Procedure

A solution of 1,1-dimethylethyl 4-({4-chloro-5-[(1-methylethyl)oxy]-2-nitrophenyl}amino)-1-piperidinecarboxylate (D84, 260 mg, 0.63 mmol) in ethanol (40 ml) was treated with Raney Nickel followed by dropwise addition over 10 minutes of a solution of hydrazine hydrate (0.315 ml, 6.3 mmol) in ethanol. The mixture was heated at 45° C. for 1 hr, then the Raney Nickel was filtered off washing with ethanol and the filtrate concentrated under vacuum to afford the title compound as a purple coloured oil (200 mg, 83%).

Workup

  1. filtrationthe Raney Nickel was filtered off
  2. washwashing with ethanol
  3. concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-c45c9dfe191c485981a7e734555c9ec7
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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