Hydrazine hydrate (1:1) → HCID 66855373, compound

HRID 2400765Notes

Reaction equation

HRID 2400765 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[CH2:10][N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=3[N+:24]([O-])=O)[C:13](=[O:27])[CH2:12]2)=[CH:4][CH:3]=1.O.NN>[Ni].C(O)C>[NH2:24][C:18]1[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:17]=1[N:14]1[CH2:15][CH2:16][N:11]([CH2:10]/[CH:9]=[CH:8]/[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH2:12][C:13]1=[O:27]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66855637HCID 66855637, compound

Product 1

HCID 66855373HCID 66855373, compoundYield 45.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Raney nickel (50% slurry in water, 200 mg) was added to a solution of the compound obtained in Step C (389 mg) in ethanol (10 ml); hydrazine hydrate (0.5 ml) was added and the reaction mixture was stirred at room temperature until gas evolution ceased (1 hour). The reaction mixture was filtered over Hyflo, the solvent removed in vacuo and the residue purified by column chromatography (2.5% methanol in ethyl acetate) to afford 1-(2-Amino-5-fluoro-phenyl)-4-[(E)-3-(4-chloro-phenyl)-allyl]-piperazin-2-one (162 mg). Retention Time LCMS 2.81 min; MS (ES+) 360/362 (M+H+).

Workup

  1. custom(1 hour)
  2. filtrationThe reaction mixture was filtered over Hyflo
  3. customthe solvent removed in vacuo
  4. customthe residue purified by column chromatography (2.5% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-666d65d0726542f0ab07a9932c94d5da
Source dataset
uspto-grants-2014_08
Patent number
US08796274B2

Reaction notes

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