Ethanol → Solifenacin Succinate

HRID 1171849

Reaction equation

HRID 1171849 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([C@@H:7]2[N:16]([C:17]([O:19][C@@H:20]3[CH:25]4[CH2:26][CH2:27][N:22]([CH2:23][CH2:24]4)[CH2:21]3)=[O:18])[CH2:15][CH2:14][C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]2=3)=[CH:5][CH:6]=1.CCO.[C:31]([OH:38])(=[O:37])[CH2:32][CH2:33][C:34]([OH:36])=[O:35]>CCOC(C)=O>[CH:1]1[CH:6]=[CH:5][C:4]([C@@H:7]2[N:16]([C:17]([O:19][C@@H:20]3[CH:25]4[CH2:24][CH2:23][N:22]([CH2:27][CH2:26]4)[CH2:21]3)=[O:18])[CH2:15][CH2:14][C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]2=3)=[CH:3][CH:2]=1.[CH2:32]([C:31]([OH:38])=[O:37])[CH2:33][C:34]([OH:36])=[O:35]

Participants

5

Reactant 3

HCID 702EthanolHCID 1110Succinic AcidHCID 154059Solifenacin

Product 1

HCID 216457Solifenacin Succinate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
30 °C

Procedure

The thus obtained solifenacin was mixed with 12 ml of EtOH, 28 ml of EtOAc and 2.74 g of succinic acid, heated, cooled to 30° C. and then again heated to 50° C. This was kept at 50° C. for 2 hours and then cooled to 0° C. spending 5 hours, and the precipitated crystals were collected by filtration, washed twice with 8 ml of EtOAc and then dried under a reduced pressure to obtain 9.013 g of solifenacin succinate.

Workup

  1. temperatureheated
  2. temperatureagain heated to 50° C
  3. temperaturecooled to 0° C.
  4. waitspending 5 hours
  5. filtrationthe precipitated crystals were collected by filtration
  6. washwashed twice with 8 ml of EtOAc
  7. customdried under a reduced pressure

Sources & evidence

ORD record
ord-b008daffcd744614946eb1f37250dec3
Source dataset
uspto-grants-2010_11
Patent number
US07829715B2

Linked notes

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