Sodium Hydroxide → Quetiapine

HRID 251397

Reaction equation

HRID 251397 reaction equation
C([O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][N:13]([C:16]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[S:20][C:19]3[CH:27]=[CH:28][CH:29]=[CH:30][C:18]=3[N:17]=2)[CH2:12][CH2:11]1)(=O)C.[OH-].[Na+]>C(O)C>[CH:24]1[CH:25]=[CH:26][C:21]2[S:20][C:19]3[CH:27]=[CH:28][CH:29]=[CH:30][C:18]=3[N:17]=[C:16]([N:13]3[CH2:14][CH2:15][N:10]([CH2:9][CH2:8][O:7][CH2:6][CH2:5][OH:4])[CH2:11][CH2:12]3)[C:22]=2[CH:23]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11487114Quetiapine acetate

Product 1

HCID 5002QuetiapineYield 98.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The residue of 11-(4-[2-(2-acetyloxyethoxy)ethyl]-1-piperazinyl]dibenzo[b,f]-1,4-thiazepine (7.8 g) was dissolved in ethanol (50 ml) and 1M NaOH solution (55 ml) was added. The mixture was stirred at room temperature for 30 min. The product was extracted into toluene (2×100 ml). Evaporation of the toluene phase gave quetiapine base (6.9 g).

Workup

  1. extractionThe product was extracted into toluene (2×100 ml)
  2. customEvaporation of the toluene phase

Sources & evidence

ORD record
ord-a5210979d7f94179863f210cad5b3ea0
Source dataset
uspto-grants-2011_01
Patent number
US07863441B2

Linked notes

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