Diisopropyl Ether → Fesoterodine fumarate

HRID 1473014Notes

Reaction equation

HRID 1473014 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].C(OC(C)C)(C)C>CC(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 7914Diisopropyl EtherHCID 444972Fumaric AcidHCID 6918558FesoterodineHCID 24885301(R)-3-(2-benzyloxy)-5-bromophenyl)-N,N-diisopropyl-3-phenylpropan-1-amine

Product 1

HCID 9849808Fesoterodine fumarateYield 130%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 42 g Fesoterodine of formula (J) in 240 ml IPA (240 ml) is added at 25° C. to 30° C. and then heated to 50° C. to 55° C. Fumaric acid (17 g) was added to the resulting mass was maintained for 30 minutes and further cooled to 25° C. to 30° C. followed by the addition of diisopropyl ether (840 ml) at 25° C. to 30° C. and maintained for 12 hours. The resulting mass was filtered, washed with diisopropyl ether (2×30 ml) and then dried under vacuum for 24 hours at 45° C. to 50° C. to afford Fesoterodine Fumarate (70 g) (Purity by HPLC: 99.98%).

Workup

  1. temperatureheated to 50° C. to 55° C
  2. temperaturewas maintained for 30 minutes
  3. temperaturefurther cooled to 25° C. to 30° C.
  4. temperaturemaintained for 12 hours
  5. filtrationThe resulting mass was filtered
  6. washwashed with diisopropyl ether (2×30 ml)
  7. customdried under vacuum for 24 hours at 45° C. to 50° C.

Sources & evidence

ORD record
ord-19836fbd2d54410daf73cfcd057f212b
Source dataset
uspto-grants-2015_04
Patent number
US09012678B2

Reaction notes

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