Cyclohexane → Fesoterodine fumarate
Reaction equation
[CH3:1][CH:2]([C:4]([O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:29][OH:30])=[CH:11][C:12]=1[C@@H:13]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:14][CH2:15][N:16]([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])=[O:5])[CH3:3].[C:31]([OH:38])(=[O:37])/[CH:32]=[CH:33]/[C:34]([OH:36])=[O:35].C1CCCCC1>C(C(C)=O)C>[CH3:3][CH:2]([C:4]([O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:29][OH:30])=[CH:11][C:12]=1[C@@H:13]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:14][CH2:15][N:16]([CH:20]([CH3:21])[CH3:22])[CH:17]([CH3:18])[CH3:19])=[O:5])[CH3:1].[CH:32](/[C:31]([OH:38])=[O:37])=[CH:33]\[C:34]([OH:36])=[O:35]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 42 g Fesoterodine in 90 ml methyl ethyl ketone was stirred with 12 g fumaric acid at 80° C. for 1 hour. This was followed by the slow addition of 30 ml cyclohexane under stirring and further stirred for 1 hour at 80° C. The solution was cooled slowly to 25° C. to 30° C. and stirred for 6 hours at the same temperature. The solution was further cooled at 0° C. to 50° C. C and stirred for overnight. The separated solid was filtered and washed with mixture of cyclohexane and methyl ethyl ketone mixture to give Fesoterodine Fumarate wherein impurity X is 0.03%.
Workup
- stirringfurther stirred for 1 hour at 80° C
- temperatureThe solution was cooled slowly to 25° C. to 30° C.
- stirringstirred for 6 hours at the same temperature
- temperatureThe solution was further cooled at 0° C. to 50° C
- stirringC and stirred for overnight
- filtrationThe separated solid was filtered
- washwashed with mixture of cyclohexane and methyl ethyl ketone mixture
Sources & evidence
- ORD record
- ord-a080d3845cfd41e99b667da5d077fcf2
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09012678B2
Reaction notes
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