Hydrazine hydrate (1:1) → HCID 69127637, compound

HRID 2064195Notes

Reaction equation

HRID 2064195 reaction equation
[C:1]([C:3]1[C:8]([CH3:9])=[CH:7][C:6]([NH:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[C:5]([N+:24]([O-])=O)[CH:4]=1)#[N:2].O.NN>C(O)C.[Ni]>[NH2:24][C:5]1[CH:4]=[C:3]([C:1]#[N:2])[C:8]([CH3:9])=[CH:7][C:6]=1[NH:10][CH:11]1[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH2:16]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 69127906HCID 69127906, compound

Product 1

HCID 69127637HCID 69127637, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

A suspension of 1,1-dimethylethyl 4-[(4-cyano-5-methyl-2-nitrophenyl)amino]-1-piperidinecarboxylate (D91) (3 mmol) in ethanol (30 mL) was treated with Raney Nickel and hydrazine hydrate (30 mmol, 1.5 g, 10 eq) under argon at room temperature. The mixture was then heated at 45° C. for 1 h. 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 (2.55 mmol, 840 mg, 85% yield). M+H 331.3, 275.2, 231.2 (full molecule and fragments for loss of tert-butyl group and loss of Boc group).

Workup

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

Sources & evidence

ORD record
ord-3a9c141b48ca4c36b38c3a5671ef0ee0
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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