HCID 178418361, compound → HCID 178490549, compound

HRID 2225544Notes

Reaction equation

HRID 2225544 reaction equation
[CH3:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:26])[CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])=[C:14]([O:24][CH3:25])[CH:13]=2)[CH2:4][CH2:3]1.[H][H]>CO.[C].[Pd]>[CH3:1][C@@H:2]1[CH2:3][CH2:4][C@H:5]([NH:8][C:9](=[O:26])[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][N:21]([CH3:22])[CH3:23])=[C:14]([O:24][CH3:25])[CH:13]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178490547HCID 178490547, compound

Product 1

HCID 178490549HCID 178490549, compoundYield 92.5%

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-(cis-4-methylcyclohexyl)-4-(2-dimethylaminoethoxy)-3-methoxycinnamamide (Example 107) in 50 ml of methanol. The solution was vigorously stirred for 16 hours under normal-pressure hydrogen gas. After reaction, 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 0.93 g of N-(cis-4-methylcyclohexyl)-3-[4-(2-dimethylaminoethoxy)-3-methoxyphenyl]propionamide (a compound of the present invention) as white crystal, 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
  4. customThe product obtained
  5. customwas recrystallized from methylene chloride/ether

Sources & evidence

ORD record
ord-96b10abe800e4004a1d5f73faf7779d3
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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