HCID 178490523, compound → HCID 178490524, compound

HRID 2225574Notes

Reaction equation

HRID 2225574 reaction equation
[CH3:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:29])[CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])=[C:14]([O:27][CH3:28])[CH:13]=2)[CH2:4][CH2:3]1>[C].[Pd].CO>[CH3:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([NH:8][C:9](=[O:29])[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])=[C:14]([O:27][CH3:28])[CH:13]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 1

HCID 178490523HCID 178490523, compound

Product 1

HCID 178490524HCID 178490524, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

Using 1.5 g of N-(trans-4-methylcyclohexyl)-4-(5-dimethylaminopentyloxy)-3-methoxycinnamamide (Example 135), 0.075 g of 10% palladium-carbon, and 100 ml of methanol, a reaction similar to that conducted in Example 147 was carried out. The product obtained was recrystallized from methylene chloride/ether, yielding 1.3 g of N-(trans-4-methylcyclohexyl)-3-[4-(5-dimethylaminopentyloxy)-3-methoxyphenyl]propionamide (a compound of the present invention) as light-greenish white crystal, which had had the following physiochemical properties:

Workup

  1. customa reaction similar to
  2. customThe product obtained
  3. customwas recrystallized from methylene chloride/ether

Sources & evidence

ORD record
ord-3540360a8eea47128d3489c4363b2ee2
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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