HCID 178418361, compound → HCID 178490507, compound

HRID 2225521Notes

Reaction equation

HRID 2225521 reaction equation
[CH3:1][N:2]([CH3:28])[CH2:3][CH2:4][CH2:5][CH2:6][N:7]([C@H:21]1[CH2:26][CH2:25][C@H:24]([CH3:27])[CH2:23][CH2:22]1)[C:8](=[O:20])[CH:9]=[CH:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([O:18][CH3:19])[CH:12]=1.[H][H]>CO.[C].[Pd]>[CH3:28][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][CH2:6][N:7]([C@H:21]1[CH2:26][CH2:25][C@H:24]([CH3:27])[CH2:23][CH2:22]1)[C:8](=[O:20])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([O:18][CH3:19])[CH:12]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178490506HCID 178490506, compound

Product 1

HCID 178490507HCID 178490507, compoundYield 91.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

0.05 g of 10% palladium-carbon was added to a solution of 1 g of N-(4-dimethylaminobutyl)-N-(trans-4-methylcyclohexyl)-4-hydroxy-3-methoxycinnamamide (Example 75) in 60 ml of methanol. Under normal-pressure hydrogen gas, the solution was reacted for 16 hours, while it was vigorously stirred. After reaction, the catalyst was filtered out, and the solvent was removed in vacuo from the filtrate, yielding 0.92 g of N-(4-dimethylaminobutyl)-N-(trans-4-methylcyclohexyl)-3-(4-hydroxy-3-methoxyphenyl)propionamide (a compound of the present invention) as a pale yellow oily oil, which had the following physiochemical properties:

Workup

  1. customAfter reaction
  2. filtrationthe catalyst was filtered out
  3. customthe solvent was removed in vacuo from the filtrate

Sources & evidence

ORD record
ord-7fad1ad9d1ee4eabac525e294b0ab22a
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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