Toluene → Quetiapine fumarate

HRID 1662950Notes

Reaction equation

HRID 1662950 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

5

Reactant 3

HCID 1140TolueneHCID 5002QuetiapineHCID 444972Fumaric Acid

Product 1

HCID 5281025Quetiapine fumarate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
20 °C

Procedure

A suspension of 1.2 g (0.0103 mol) of fumaric acid in 10 ml of acetone is brought to the boil. 40 ml of a toluene solution containing 7.53 g (0.0196 mol) of pure quetiapine base is added to the boiling suspension. An oily suspension is formed, which crystallizes under boil during 3 to 4 minutes. Reflux is maintained for 5 minutes and then the suspension is cooled to 20° C. and stirred for 60 minutes. Precipitated crystalline quetiapine hemifumarate is isolated by filtration and dried.

Workup

  1. additionis added to the boiling suspension
  2. customAn oily suspension is formed
  3. customwhich crystallizes under boil during 3 to 4 minutes
  4. temperatureReflux
  5. temperatureis maintained for 5 minutes

Sources & evidence

ORD record
ord-23dfa716d1b844f8a8bdd435bb908e4f
Source dataset
uspto-grants-2011_10
Patent number
US08034805B2

Reaction notes

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