Chlorpromazine hydrochloride → Chlorpromazine

HRID 234882Notes

Reaction equation

HRID 234882 reaction equation
Cl.[Cl:2][C:3]1[CH:16]=[CH:15][C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[N:6]([CH2:17][CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])[C:5]=2[CH:4]=1.[OH-].[Na+]>>[Cl:2][C:3]1[CH:16]=[CH:15][C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[N:6]([CH2:17][CH2:18][CH2:19][N:20]([CH3:21])[CH3:22])[C:5]=2[CH:4]=1

Participants

3

Reactant 2

HCID 6240Chlorpromazine hydrochlorideHCID 14798Sodium Hydroxide

Product 1

HCID 2726ChlorpromazineYield 98.2%

Procedure

3.56 g (10 mmol) of 2-chloro-10-(3-dimethylaminopropyl) phenothiazine hydrochloride are suspended in 15 ml of a 1N sodium hydroxide solution. The amine freed is extracted with diethyl ether. The organic phase is decanted and dried over sodium sulfate and then evaporated to dryness to yield 3.13 g of an oil corresponding to the expected product.

Workup

  1. extractionThe amine freed is extracted with diethyl ether
  2. customThe organic phase is decanted
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-8e710455d9a6425c81dc3d577c7506a8
Source dataset
uspto-grants-1997_01
Patent number
US05597819

Reaction notes

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