Acetone → Carvedilol phosphate hemihydrate

HRID 2356839Notes

Reaction equation

HRID 2356839 reaction equation
CC(C)=[O:3].[CH3:5][O:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][NH:16][CH2:17][CH:18]([OH:34])[CH2:19][O:20][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[NH:33][C:32]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:26]=12.[OH:35][P:36]([OH:39])([OH:38])=[O:37]>O>[CH3:5][O:6][C:7]1[C:12]([O:13][CH2:14][CH2:15][NH:16][CH2:17][CH:18]([OH:34])[CH2:19][O:20][C:21]2[C:26]3[C:27]4[C:32]([NH:33][C:25]=3[CH:24]=[CH:23][CH:22]=2)=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:5][O:6][C:7]1[C:12]([O:13][CH2:14][CH2:15][NH:16][CH2:17][CH:18]([OH:34])[CH2:19][O:20][C:21]2[C:26]3[C:27]4[C:32]([NH:33][C:25]=3[CH:24]=[CH:23][CH:22]=2)=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH2:3].[OH:37][P:36]([OH:39])([OH:38])=[O:35].[OH:37][P:36]([OH:39])([OH:38])=[O:35]

Participants

5

Reactant 3

HCID 180Acetone2×HCID 1004Phosphoric AcidHCID 2585Carvedilol

Product 1

HCID 11954344Carvedilol phosphate hemihydrate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A suitable reactor is charged with acetone. The acetone solution is sequentially charged with carvedilol and water. Upon addition of the water, the slurry dissolves quickly. To the solution is added aqueous H3PO4. The reaction mixture is stirred at room temperature and carvedilol dihydrogen phosphate seeds are added in one portion. The solid precipitate formed is stirred, then filtered and the collected cake is washed with aqueous acetone. The cake is dried under vacuum to a constant weight. The cake is weighed and stored in a polyethylene container.

Workup

  1. dissolutionthe slurry dissolves quickly
  2. customThe solid precipitate formed
  3. stirringis stirred
  4. filtrationfiltered
  5. washthe collected cake is washed with aqueous acetone
  6. customThe cake is dried under vacuum to a constant weight

Sources & evidence

ORD record
ord-e89187c1a8cd45c583deac093156bbaf
Source dataset
uspto-grants-2010_07
Patent number
US07759384B2

Reaction notes

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