HCID 53636533, compound → HCID 66758142, compound

HRID 242514Notes

Reaction equation

HRID 242514 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:34])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH:16]=[C:17]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[CH2:21][O:20][C:19]4[CH:28]=[CH:29][C:30]([C:32]#[N:33])=[CH:31][C:18]3=4)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1>CCO.[Ni]>[NH2:33][CH2:32][C:30]1[CH:29]=[CH:28][C:19]2[O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:17](=[CH:16][CH2:15][CH2:14][N:11]3[CH2:12][CH2:13][C:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)([OH:34])[CH2:9][CH2:10]3)[C:18]=2[CH:31]=1

Participants

4

Reactant 1

HCID 53636533HCID 53636533, compound

Product 1

HCID 66758142HCID 66758142, compoundYield 33.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-(4-chlorophenyl)-1-[3-(2-cyano-6,11-dihydrodibenz[b,e]oxepin-11-ylidene)propyl]piperidin-4-ol (380 mg) in EtOH (20 ml) were added Raney nickel (50% slurry in water, 60 mg), and the mixture was hydrogenated at 15 psi for 2 hours. The mixture was filtered through the celite and distilled off under reduced pressure. The residue was purified by silica gel chromatography eluting with dichloromethane-methanol-aqueous ammonium (95:5:1) to give the titled compound (130 mg).

Workup

  1. filtrationThe mixture was filtered through the celite
  2. distillationdistilled off under reduced pressure
  3. customThe residue was purified by silica gel chromatography
  4. washeluting with dichloromethane-methanol-aqueous ammonium (95:5:1)

Sources & evidence

ORD record
ord-dae9afc181ce47bca64c7c8beb7843ae
Source dataset
uspto-grants-2014_02
Patent number
US08653096B2

Reaction notes

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