Hydrazine hydrate (1:1) → HCID 59863015, compound

HRID 2064085Notes

Reaction equation

HRID 2064085 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]([F:15])([F:14])[F:13])=[CH:6][C:5]=1[NH:16][CH:17]1[CH2:22][CH2:21][N:20]([CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH2:19][CH2:18]1)([O-])=O.O.NN>C(O)C.[Ni]>[O:26]1[CH2:27][CH2:28][CH:23]([N:20]2[CH2:19][CH2:18][CH:17]([NH:16][C:5]3[C:4]([NH2:1])=[CH:9][CH:8]=[C:7]([O:10][CH2:11][C:12]([F:13])([F:15])[F:14])[CH:6]=3)[CH2:22][CH2:21]2)[CH2:24][CH2:25]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59863017HCID 59863017, compound

Product 1

HCID 59863015HCID 59863015, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A stirred solution of N-{2-nitro-5-[(2,2,2-trifluoroethyl)oxy]phenyl}-1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine (D56, 210 mg, 0.52 mmol) in ethanol (15 ml) at room temperature under argon was treated with Raney Nickel (20 mg) followed by dropwise addition of hydrazine hydrate (0.16 ml, 5.0 mmol). The mixture was maintained at room temperature for 1 hr, then filtered through Kieselguhr and the filtrate concentrated under vacuum to leave the title compound as a pale grey solid (190 mg, 98%).

Workup

  1. filtrationfiltered through Kieselguhr
  2. concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-07ce4a4eeafd46c5b88891c94a43ac5c
Source dataset
uspto-grants-2012_10
Patent number
US08288413B2

Reaction notes

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