Diethyl Ether → Quetiapine Besylate

HRID 421568

Reaction equation

HRID 421568 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[S:15][C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[C:7]([N:16]3[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][O:24][CH2:25][CH2:26][OH:27])[CH2:18][CH2:17]3)[C:5]=2[CH:6]=1.[C:28]1([S:34]([OH:37])(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(OCC)C>CC(C)=O>[CH:1]1[CH:2]=[CH:3][C:4]2[S:15][C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[C:7]([N:16]3[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][O:24][CH2:25][CH2:26][OH:27])[CH2:18][CH2:17]3)[C:5]=2[CH:6]=1.[S:34]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([O-:37])(=[O:36])=[O:35]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 5002QuetiapineHCID 7371Benzenesulfonic Acid

Product 1

HCID 131729401Quetiapine Besylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
42.5 °C

Procedure

Quetiapine free base (5.0 g) was dissolved in acetone (50 ml) at room temperature. This was followed by the addition of benzene sulfonic acid (2.0 g) at 30 to 35° C. The resulting mass was heated at 40-45° C. and maintained for 30 minutes. The resulting mass was cooled at 25-30° C. This was followed by the addition of diethyl ether (50 ml) and stirred for 3 hours. The precipitated product was collected by filtration under nitrogen and washed with diethyl ether (25 ml) and dried under vacuum to give the title compound as off white powder (5.94 g).

Workup

  1. temperaturemaintained for 30 minutes
  2. temperatureThe resulting mass was cooled at 25-30° C
  3. filtrationThe precipitated product was collected by filtration under nitrogen
  4. washwashed with diethyl ether (25 ml)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-c659196a311943ae9e9e81e03e4b6e1a
Source dataset
uspto-grants-2012_01
Patent number
US08101597B2

Linked notes

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