6-Piperazin-1-ylbenzo[b][1,4]benzothiazepine;hydrochloride → Norquetiapine

HRID 1941757Notes

Reaction equation

HRID 1941757 reaction equation
Cl.[N:2]1([C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[S:12][C:11]3[CH:19]=[CH:20][CH:21]=[CH:22][C:10]=3[N:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1>C1(C)C=CC=CC=1>[N:2]1([C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[S:12][C:11]3[CH:19]=[CH:20][CH:21]=[CH:22][C:10]=3[N:9]=2)[CH2:3][CH2:4][NH:5][CH2:6][CH2:7]1

Participants

3

Reactant 1

HCID 162023916-Piperazin-1-ylbenzo[b][1,4]benzothiazepine;hydrochloride

Product 1

HCID 11369918Norquetiapine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The above procedure was repeated for an additional four aqueous solutions of 11-piperazin-1-yldibenzo[b,f][1,4]thiazepine hydrochloride and the five resulting toluene solutions were combined and evaporated to dryness on a rotary evaporator. The resulting hard solid was then charged to a jacketed vessel and slurried with methyl-t-butyl ether (MTBE) (500 mL). The resulting slurry was stirred overnight at ambient temperature and then cooled to 5° C. and held for 4 h. The solid 11-piperazin-1-yldibenzo[b,f][1,4]thiazepine product was isolated on a no. 3 sinter and washed with 200 mL of cold MTBE. The cake was dried in a vacuum oven overnight at 60° C. yielding 373 g of product.

Workup

  1. customevaporated to dryness on a rotary evaporator
  2. additionThe resulting hard solid was then charged to a jacketed vessel
  3. temperaturecooled to 5° C.
  4. waitheld for 4 h

Sources & evidence

ORD record
ord-49342d5482bb4e368c32efa1a2bf9d64
Source dataset
uspto-grants-2013_03
Patent number
US08389510B2

Reaction notes

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