Cyclohexane → Fesoterodine fumarate

HRID 1473008Notes

Reaction equation

HRID 1473008 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(N(CC[C@@H](C1C=C(Br)C=CC=1OCC1C=CC=CC=1)C1C=CC=CC=1)C(C)C)(C)C.[C:62]([OH:69])(=[O:68])/[CH:63]=[CH:64]/[C:65]([OH:67])=[O:66].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:63](/[C:62]([OH:69])=[O:68])=[CH:64]\[C:65]([OH:67])=[O:66]

Participants

6

Reactant 4

HCID 8078CyclohexaneHCID 444972Fumaric AcidHCID 6918558FesoterodineHCID 24885301(R)-3-(2-benzyloxy)-5-bromophenyl)-N,N-diisopropyl-3-phenylpropan-1-amine

Product 1

HCID 9849808Fesoterodine fumarate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of 42 g Fesoterodine of formula (J) 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.

Workup

  1. stirringfurther stirred for 1 hour at 80° C
  2. temperatureThe solution was cooled slowly to 25° C. to 30° C.
  3. stirringstirred for 6 hours at the same temperature
  4. temperatureThe solution was further cooled at 0° C. to 50° C
  5. stirringC and stirred for overnight
  6. filtrationThe separated solid was filtered
  7. washwashed with mixture of cyclohexane and methyl ethyl ketone mixture

Sources & evidence

ORD record
ord-f4e1315d37c740e1b01e9dce77eb6e48
Source dataset
uspto-grants-2015_04
Patent number
US09012678B2

Reaction notes

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