HCID 67742921, compound → HCID 18993326, compound

HRID 375572Notes

Reaction equation

HRID 375572 reaction equation
Cl.[C:2]1([C:8]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:9][CH:10]2[CH2:15][CH2:14][CH2:13][N:12]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]4[O:24][CH2:25][O:26][C:20]=4[CH:19]=3)[CH2:11]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCO.[Pd]>[C:27]1([CH:8]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][CH:10]2[CH2:15][CH2:14][CH2:13][N:12]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]4[O:24][CH2:25][O:26][C:20]=4[CH:19]=3)[CH2:11]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 1

HCID 67742921HCID 67742921, compound

Product 1

HCID 18993326HCID 18993326, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-(2,2-diphenyl-1-ethenyl)-1-(3,4-methylenedioxyphenethyl)piperidine hydrochloride (135 mg) (Example 14) in EtOH (20 ml) was stirred at 40° C. under a hydrogen atmosphere of 45 psi in the presence of 10% palladium on charcoal. The mixture was filtered and the filtrate evaporated. The residue was partitioned between dichloromethane and 2M aqueous sodium hydroxide solution and the organic layer was dried over sodium sulphate and evaporated. The residue was purified by chromatography on silica using dichloromethane plus 2.5% methanol as eluant. Appropriate fractions were combined and evaporated to give the title compound as a colourless oil (60 mg, 50%) which was characterised as a hemihydrate.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated
  3. customThe residue was partitioned between dichloromethane and 2M aqueous sodium hydroxide solution
  4. dry with materialthe organic layer was dried over sodium sulphate
  5. customevaporated
  6. customThe residue was purified by chromatography on silica
  7. customevaporated

Sources & evidence

ORD record
ord-a7312e9b9ad8469baf078170b6f21651
Source dataset
uspto-grants-1996_01
Patent number
US05486527

Reaction notes

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