Toluene → Quetiapine fumarate

HRID 1662946Notes

Reaction equation

HRID 1662946 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 1.62 g (0.014 mol) of fumaric acid in 100 ml of acetone is brought to the boil. 100 ml of a toluene solution containing 10.77 g (0.028 mol) of pure quetiapine base is added to the boiling suspension, and the reaction mixture is heated to the boil for another 5 minutes. The precipitated crystalline product is cooled to approximately 20° C., and the reaction mixture is stirred for another 60 minutes. The precipitated crystalline quetiapine hemifumarate is filtered, washed, and dried.

Workup

  1. additionis added to the boiling suspension
  2. temperaturethe reaction mixture is heated to the boil for another 5 minutes
  3. filtrationThe precipitated crystalline quetiapine hemifumarate is filtered
  4. washwashed
  5. customdried

Sources & evidence

ORD record
ord-27bd8192fbca418e97e5772d91ec478f
Source dataset
uspto-grants-2011_10
Patent number
US08034805B2

Reaction notes

Loading…