Hydrazine hydrate (1:1) → 5-Chloro-4-(difluoromethyl)-N-[1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]-1,2-benzenediamine

HRID 2064200Notes

Reaction equation

HRID 2064200 reaction equation
[Cl:1][C:2]1[C:3]([CH:24]([F:26])[F:25])=[CH:4][C:5]([N+:21]([O-])=O)=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[CH2:11][CH2:10]2)[CH:7]=1.O.NN>C(O)C.[Ni]>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][CH:9]2[CH2:10][CH2:11][N:12]([CH:15]3[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)[CH2:13][CH2:14]2)[C:5]([NH2:21])=[CH:4][C:3]=1[CH:24]([F:26])[F:25]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59850155N-[5-Chloro-4-(difluoromethyl)-2-nitrophenyl]-1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine

Product 1

HCID 598501795-Chloro-4-(difluoromethyl)-N-[1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]-1,2-benzenediamineYield 59.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A stirred suspension of N-[5-chloro-4-(difluoromethyl)-2-nitrophenyl]-1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine (D97, 330 mg, 0.84 mmol) in ethanol (20 ml) at room temperature under argon was treated with Raney Nickel (20 mg) followed by dropwise addition of hydrazine hydrate (0.25 ml, 8.0 mmol). The mixture was maintained at room temperature for 30 minutes, then heated at 45° C. for 1 hr. The mixture was filtered through a pad of Kieselguhr and the filtrate concentrated under vacuum to leave the title compound as a yellow solid (180 mg of ˜88% purity, 59% yield).

Workup

  1. temperatureheated at 45° C. for 1 hr
  2. filtrationThe mixture was filtered through a pad of Kieselguhr
  3. concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-0668d55273384e7ebd2fe40e9e7e395e
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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