1-methyl-6-[3-(N-cyclohexyl-N-methylaminocarbonyl)-propoxy]carbostyril → 1-methyl-6-[3-(N-cyclohexyl-N-methylaminocarbonyl)propoxy]-3,4-dihydrocarbostyril

HRID 1154960Notes

Reaction equation

HRID 1154960 reaction equation
[CH3:1][N:2]1[C:12]2[C:7](=[CH:8][C:9]([O:13][CH2:14][CH2:15][CH2:16][C:17]([N:19]([CH3:26])[CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[O:18])=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:3]1=[O:4]>CO.[Pd]>[CH3:1][N:2]1[C:12]2[C:7](=[CH:8][C:9]([O:13][CH2:14][CH2:15][CH2:16][C:17]([N:19]([CH3:26])[CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[O:18])=[CH:10][CH:11]=2)[CH2:6][CH2:5][C:3]1=[O:4]

Participants

4

Reactant 1

HCID 155729251-methyl-6-[3-(N-cyclohexyl-N-methylaminocarbonyl)-propoxy]carbostyril

Product 1

HCID 155729261-methyl-6-[3-(N-cyclohexyl-N-methylaminocarbonyl)propoxy]-3,4-dihydrocarbostyrilYield 67.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2.8 g of 1-methyl-6-[3-(N-methyl-N-cyclohexylaminocarbonyl)propoxy]carbostyril in 50 ml of methanol is added 0.1 g of palladium black, and the mixture is reacted at 50° C. under hydrogen pressure of 2.5 atm. for 8 hours. After the reaction, the catalyst is filtered out and the filtrate is concentrated and evaporated to dryness. The residue is recrystallized from ligroin to obtain 1.9 g of 1-methyl-6-[3-(N-methyl-N-cyclohexylaminocarbonyl)propoxy]-3,4-dihydrocarbostyril in the form of colorless needle-like crystals with melting point of 104.5°-106.5° C.

Workup

  1. customthe mixture is reacted at 50° C. under hydrogen pressure of 2.5 atm. for 8 hours
  2. customAfter the reaction
  3. filtrationthe catalyst is filtered out
  4. concentrationthe filtrate is concentrated
  5. customevaporated to dryness
  6. customThe residue is recrystallized from ligroin

Sources & evidence

ORD record
ord-2953abc5fd4c4153ba46f093d12790aa
Source dataset
uspto-grants-1981_11
Patent number
US04298739

Reaction notes

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