HCID 9801910, compound → HCID 9927277, compound

HRID 380573Notes

Reaction equation

HRID 380573 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([CH2:14][NH:15][C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH3:25])=[O:17])[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>[OH-].[OH-].[Pd+2].C(O)(=O)C.CO>[C:26]1([C:11]2([CH2:14][NH:15][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH3:25])=[O:17])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 2

HCID 9801910HCID 9801910, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9927277HCID 9927277, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1.3 g (3.1 mmol) of 1-N-Benzyl-4-phenyl-4-(3-(2-methoxyphenyl)-3-oxo-2-azaprop-1-yl)piperidine (Example 1), 100 mg of Pearlman's catalyst (palladium hydroxide on carbon, purchased from Aldrich Chemical Co., Milwaukee, Wis.) and 3 drops of acetic acid in 20 mL of methanol was stirred in a hydrogen atmosphere (50 psi) for 18 hr. The reaction mixture was filtered and the filtrate was concentrated to afford the title compound.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d0b067c17a154133b18fef4d0d5f615a
Source dataset
uspto-grants-2001_10
Patent number
US06303637B1

Reaction notes

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