HCID 178418361, compound → HCID 178490120, compound

HRID 2225550Notes

Reaction equation

HRID 2225550 reaction equation
[CH3:1][N:2]([CH3:35])[CH2:3][CH2:4][N:5]([C@H:28]1[CH2:33][CH2:32][C@H:31]([CH3:34])[CH2:30][CH2:29]1)[C:6]([CH:8]=[CH:9][CH:10]=[CH:11][C:12]1[CH:17]=[CH:16][C:15]([O:18]CC2C=CC=CC=2)=[C:14]([O:26][CH3:27])[CH:13]=1)=[O:7].[H][H]>CO.[C].[Pd]>[CH3:35][N:2]([CH3:1])[CH2:3][CH2:4][N:5]([C@H:28]1[CH2:33][CH2:32][C@H:31]([CH3:34])[CH2:30][CH2:29]1)[C:6](=[O:7])[CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([O:26][CH3:27])[CH:13]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178490121HCID 178490121, compound

Product 1

HCID 178490120HCID 178490120, compoundYield 67.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

3.81 g of N-(2-dimethylaminoethyl)-N-(trans-4-methylcyclohexyl)-4-(4-benzyloxy-3-methoxyphenyl)-1,3-butadiene-1-carboxamide (Example 113) was dissolved in 100 ml of methanol. 0.2 g of 10% palladium-carbon was added to the solution. The solution was vigorously stirred at room temperature under normal-pressure hydrogen gas. After 18 hours, the reaction was ceased, and the catalyst was filtered out. The solvent was removed in vacuo from the filtrate, yielding 2.1 g of N-(2-dimethylaminoethyl)-N-(trans-4-methylcyclohexyl)-5-(4-hydroxy-3-methoxyphenyl)valeramide (a compound of the present invention) as a pale yellow oil, which had the following physiochemical properties:

Workup

  1. filtrationthe catalyst was filtered out
  2. customThe solvent was removed in vacuo from the filtrate

Sources & evidence

ORD record
ord-bf2faa34bfa24d55bd25a1e559f5c2db
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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