HCID 178418361, compound → HCID 178490512, compound

HRID 2225524Notes

Reaction equation

HRID 2225524 reaction equation
[CH3:1][N:2]([CH3:26])[CH2:3][CH2:4][N:5]([C@H:19]1[CH2:24][CH2:23][C@H:22]([CH3:25])[CH2:21][CH2:20]1)[C:6](=[O:18])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([O:16][CH3:17])[CH:10]=1.[H][H]>CO.[C].[Pd]>[CH3:26][N:2]([CH3:1])[CH2:3][CH2:4][N:5]([C@H:19]1[CH2:24][CH2:23][C@H:22]([CH3:25])[CH2:21][CH2:20]1)[C:6](=[O:18])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([O:16][CH3:17])[CH:10]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178490510HCID 178490510, compound

Product 1

HCID 178490512HCID 178490512, compoundYield 93.5%

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-(2-dimethylaminoethyl)-N-(trans-4-methylcyclohexyl)-4-hydroxy-3-methoxycinnamamide (Example 79) in 60 ml of methanol. Under normal-pressure hydrogen gas, the solution was vigorously stirred. After 16 hours, the reaction was ceased, the catalyst was filtered out, and the solvent was removed in vacuo from the filtrate. The product obtained was recrystallized from methylene chloride/ether, yielding 0.94 g of N-(2-dimethylaminoethyl)-N-(trans-4-methylcyclohexyl)-3-(4-hydroxy-3-methoxyphenyl)propionamide (a compound of the present invention) as white crystal, which had the following physiochemical properties:

Workup

  1. filtrationthe catalyst was filtered out
  2. customthe solvent was removed in vacuo from the filtrate
  3. customThe product obtained
  4. customwas recrystallized from methylene chloride/ether

Sources & evidence

ORD record
ord-5082e685ce944bb58a0432237cf4f56c
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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