Hydrazine → HCID 74931736, compound

HRID 1095136Notes

Reaction equation

HRID 1095136 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:41])[C:10]3([CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C:13](=[O:23])[NH:12][CH:11]3[C:24]3[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:25]=3[O:31][C:32]3[CH:37]=[CH:36][C:35]([N+:38]([O-])=O)=[CH:34][CH:33]=3)[C:5]2=[CH:4][CH:3]=1.NN>C(O)C.[Ni]>[NH2:38][C:35]1[CH:36]=[CH:37][C:32]([O:31][C:25]2[CH:26]=[CH:27][C:28]([Cl:30])=[CH:29][C:24]=2[CH:11]2[C:10]3([C:5]4[C:6](=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=4)[NH:8][C:9]3=[O:41])[CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=3)[CH2:14][C:13](=[O:23])[NH:12]2)=[CH:33][CH:34]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 74931735HCID 74931735, compound

Product 1

HCID 74931736HCID 74931736, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of racemic(2′R, 3R, 4′S)-6-chloro-2′-[5-chloro-2-(4-nitro-phenoxy)-phenyl]-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (0.31 g, 0.51 mmol) in anhydrous ethanol (20 mL) was added Raney-Ni (0.6 g) and anhydrous hydrazine (0.118 g, 2.54 mmol). The reaction mixture was stirred at room temperature for 0.5 h, then filtered through a short pad of celite. The filtrate was concentrated. The residue was partitioned between ethyl acetate and water. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate three times. The organic layers were combined, washed with water, brine, and dried over MgSO4, and concentrated to give racemic(2′R, 3R, 4′S)-2′-[2-(4-amino-phenoxy)-5-chloro-phenyl]-6-chloro-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield 0.28 g, 95%).

Workup

  1. filtrationfiltered through a short pad of celite
  2. concentrationThe filtrate was concentrated
  3. customThe residue was partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate three times
  6. washwashed with water, brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-25fc6d01f73f42948af09f922a00d8ba
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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