Ethyl Acetate → Carvedilol

HRID 646649Notes

Reaction equation

HRID 646649 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH2:10][CH2:11][N:12]([CH2:20][CH:21]([OH:37])[CH2:22][O:23][C:24]2[C:29]3[C:30]4[C:35]([NH:36][C:28]=3[CH:27]=[CH:26][CH:25]=2)=[CH:34][CH:33]=[CH:32][CH:31]=4)CC2C=CC=CC=2)=[CH:7][CH:6]=[CH:5][CH:4]=1.C(OCC)(=O)C>[Pd].O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH2:11][NH:12][CH2:20][CH:21]([OH:37])[CH2:22][O:23][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[NH:36][C:35]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:29]=12

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 110383641-{benzyl[2-(2-methoxyphenoxy)ethyl]amino}-3-(9H-carbazol-4-yloxy)propan-2-ol

Product 1

HCID 2585CarvedilolYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
47.5 °C

Procedure

Benzyl carvedilol (205 g) obtained in step 3 was charged to ethyl acetate (2400 ml) and water (240 ml). The contents were stirred and 10% palladium on carbon (20 g) was added at room temperature. Hydrogen gas was bubbled at room temperature. The temperature was raised to 45-50° C. and bubbling was continued for 8 hours. The reaction mass was filtered to remove the catalyst and the filtrate was concentrated to remove solvent (about 2 L). The contents were chilled to 15-20° C., filtered and washed with chilled ethyl acetate (50 ml) to give carvedilol (140 g) (84%).

Workup

  1. customHydrogen gas was bubbled at room temperature
  2. custombubbling
  3. filtrationThe reaction mass was filtered
  4. customto remove the catalyst
  5. concentrationthe filtrate was concentrated
  6. customto remove solvent (about 2 L)
  7. temperatureThe contents were chilled to 15-20° C.
  8. filtrationfiltered
  9. washwashed with chilled ethyl acetate (50 ml)

Sources & evidence

ORD record
ord-bba4d6cd52834d7a810f1c8ea019888d
Source dataset
uspto-grants-2010_04
Patent number
US07705163B2

Reaction notes

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