Ethanol → Solifenacin Succinate

HRID 1171850

Reaction equation

CCO.[C:4]([OH:11])(=[O:10])[CH2:5][CH2:6][C:7]([OH:9])=[O:8].[N:12]12[CH2:19][CH2:18][CH:15]([CH2:16][CH2:17]1)[C@@H:14]([O:20][C:21]([N:23]1[CH2:32][CH2:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:22])[CH2:13]2>CCOC(C)=O>[CH:36]1[CH:37]=[CH:38][C:33]([C@@H:24]2[N:23]([C:21]([O:20][C@@H:14]3[CH:15]4[CH2:16][CH2:17][N:12]([CH2:19][CH2:18]4)[CH2:13]3)=[O:22])[CH2:32][CH2:31][C:30]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]2=3)=[CH:34][CH:35]=1.[CH2:5]([C:4]([OH:11])=[O:10])[CH2:6][C:7]([OH:9])=[O:8]

Participants

Conditions

Temperature: 50 °C

Procedure

A 6 ml portion of EtOH, 14 ml of EtOAc and 1.30 g of succinic acid were added to the thus obtained (1RS)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid (3R)-quinuclidin-3-yl ester, dissolved by heating and cooled to 50° C., and then 0.003 g of seed crystal of solifenacin succinate produced in the same manner as in Example 1A was added thereto. This mixture was 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 10 ml of EtOAc and then dried under a reduced pressure to obtain 2.855 g of solifenacin succinate as colorless crystals.

Workup

dissolutiondissolved
temperatureby heating

Sources & evidence

ORD record: ord-6462d808f7b140c1ba5f45f1e73a07ed
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07829715B2

Linked notes

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