HCID 86746607, compound → HCID 15382031, compound

HRID 1613305Notes

Reaction equation

HRID 1613305 reaction equation
[C:1]1(/[C:7](/[C:31]#[C:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:8]\[C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:30])[C:18]3[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=3)[CH2:13][CH2:12]2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>N1C2C(=CC=CC=2)C=CC=1.CO>[C:1]1(/[C:7](/[CH:31]=[CH:32]\[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[CH:8]/[C:9]([N:11]2[CH2:12][CH2:13][N:14]([C:17](=[O:30])[C:18]3[CH:19]=[C:20]([O:28][CH3:29])[C:21]([O:26][CH3:27])=[C:22]([O:24][CH3:25])[CH:23]=3)[CH2:15][CH2:16]2)=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 86746607HCID 86746607, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15382031HCID 15382031, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 7047QuinolineCatalystHCID 887MethanolSolvent

Procedure

0.25 g of 10% w/w palladium-on-barium sulfate and two drops of quinoline were added to 5 ml of a methanol solution containing 0.250 g of 1-[(E)-3,5-diphenylpent-2-en-4-ynoyl]-4-(3,4,5-trimethoxybenzoyl)piperazine (prepared as described in Example 58). Hydrogen gas was introduced into the reaction mixture at room temperature and at atmospheric pressure. The reaction mixture was then shaken for 15 hours, after which the catalyst was filtered off and the solvent was removed by distillation under reduced pressure. The residue was subjected to moderate pressure liquid chromatography using a Lobar B column. 0.153 g of the title compound was obtained as a powder from those fractions eluted with mixtures of methylene chloride and ethyl acetate ranging from 3:2 to 1:3 by volume.

Workup

  1. filtrationafter which the catalyst was filtered off
  2. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-9254f814e2ac4e6887260a01114cfd1c
Source dataset
uspto-grants-1993_03
Patent number
US05192766

Reaction notes

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