Isopropanol → Carvedilol

HRID 254875Notes

Reaction equation

HRID 254875 reaction equation
[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][CH2:13][CH:14]([OH:30])[CH2:15][O:16][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[NH:29][C:28]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:22]=12.C([O-])(=O)C1C(=CC=CC=1)O.CC(O)C.[OH-].[Na+]>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][CH2:13][CH:14]([OH:30])[CH2:15][O:16][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[NH:29][C:28]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:22]=12

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 178489624HCID 178489624, compound

Product 1

HCID 2585CarvedilolYield 91.21%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of Carvedilol salicylate (36.0 g, 66.18 mmole) and 2-propanol (108 ml) is heated to 50° C. to 55° C. To this, a solution of sodium hydroxide (4.5 g) in water (36 ml) is added slowly in about 30 minutes. The solution is then stirred at 65° C. to 70° C. for 15 minutes and filtered, followed by two 18 ml wash with hot (55° C. to 60° C.) 2-propanol. The filtrate is cooled to 30° C. to 40° C., 18 ml of water is added and stirred at 25° C. to 35° C. for 3 hours. The precipitated product is filtered, followed by two 30 ml wash with water. The wet product dried at 50° C. to 55° C. till constant weight gives 24.5 g of Carvedilol (Yield=91.21%).

Workup

  1. temperatureis heated to 50° C. to 55° C
  2. filtrationfiltered
  3. washwash with hot (55° C. to 60° C.) 2-propanol
  4. temperatureThe filtrate is cooled to 30° C. to 40° C.
  5. addition18 ml of water is added
  6. stirringstirred at 25° C. to 35° C. for 3 hours
  7. filtrationThe precipitated product is filtered
  8. washwash with water
  9. customThe wet product dried at 50° C. to 55° C. till constant weight

Sources & evidence

ORD record
ord-4172ab5bf34d4ead906bcc14a669d4b2
Source dataset
uspto-grants-2011_01
Patent number
US07875730B2

Reaction notes

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