Toluene → Quetiapine fumarate

HRID 1662951Notes

Reaction equation

[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].C1(C)C=CC=CC=1.[CH:16]1[CH:17]=[CH:18][C:19]2[S:30][C:29]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[N:23]=[C:22]([N:31]3[CH2:36][CH2:35][N:34]([CH2:37][CH2:38][O:39][CH2:40][CH2:41][OH:42])[CH2:33][CH2:32]3)[C:20]=2[CH:21]=1>CC(C)=O>[CH2:33]1[N:34]([CH2:37][CH2:38][O:39][CH2:40][CH2:41][OH:42])[CH2:35][CH2:36][N:31]([C:22]2[C:20]3[C:19](=[CH:18][CH:17]=[CH:16][CH:21]=3)[S:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=2)[CH2:32]1.[CH2:33]1[N:34]([CH2:37][CH2:38][O:39][CH2:40][CH2:41][OH:42])[CH2:35][CH2:36][N:31]([C:22]2[C:20]3[C:19](=[CH:18][CH:17]=[CH:16][CH:21]=3)[S:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=2)[CH2:32]1.[CH:2](/[C:1]([OH:8])=[O:7])=[CH:3]\[C:4]([OH:6])=[O:5]

Participants

Conditions

Temperature: 20 °C

Procedure

A suspension of 0.8 g (0.007 mol) of fumaric acid in 120 ml of acetone is brought to the boil. 30 ml of a toluene solution containing 5.06 g (0.0132 mol) of pure quetiapine base is added to the boiling suspension and the reaction mixture is stirred under boil for another 5 minutes. The precipitated crystalline product is cooled to approximately 20° C. and stirred for another 60 minutes. Precipitated crystalline quetiapine hemifumarate is isolated by filtration, washed and dried.

Workup

additionis added to the boiling suspension
stirringstirred for another 60 minutes

Sources & evidence

ORD record: ord-2b78fc8110ea4e529aae4ee5b687e908
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08034805B2

Reaction notes

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