Hydrogen Bromide → Quetiapine Hydrobromide

HRID 421566Notes

Reaction equation

HRID 421566 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.[BrH:28]>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.[BrH:28]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 5002Quetiapine

Product 1

HCID 24748093Quetiapine Hydrobromide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
22.5 °C

Procedure

Quetiapine free base (5.0 g) was dissolved in acetone (50 ml) at room temperature. This was followed by addition of 48% aqueous hydrobromic acid (2 ml) at 30 to 35° C. The resulting solution was stirred for 1 hour at 20 to 25° C. Next, acetone was distilled under vacuum at 40 to 45° C. followed by addition of acetone (50 ml) and distilled under vacuum at 40 to 45° C. till complete removal. Next, acetone (50 ml) and diisopropyl ether (50 ml) were added at 40 to 45° C. The resulted mass was refluxed for 30 minutes and cooled at 20 to 25° C. and further stirred for 2.5 hours. The precipitated product was collected by filtration, washed with diisopropyl ether (25 ml) and dried to give the title compound as white powder (3.8 g).

Workup

  1. distillationNext, acetone was distilled under vacuum at 40 to 45° C.
  2. additionfollowed by addition of acetone (50 ml)
  3. distillationdistilled under vacuum at 40 to 45° C. till complete removal
  4. additionNext, acetone (50 ml) and diisopropyl ether (50 ml) were added at 40 to 45° C
  5. temperatureThe resulted mass was refluxed for 30 minutes
  6. temperaturecooled at 20 to 25° C.
  7. stirringfurther stirred for 2.5 hours
  8. filtrationThe precipitated product was collected by filtration
  9. washwashed with diisopropyl ether (25 ml)
  10. customdried

Sources & evidence

ORD record
ord-53e519a6384e42af952748f71bb5e7de
Source dataset
uspto-grants-2012_01
Patent number
US08101597B2

Reaction notes

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