Chlorpromazine hydrochloride → Chlorpromazine

HRID 2256197Notes

Reaction equation

HRID 2256197 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-54649aac1e7b49639dc875d5bdd33045
Source dataset
uspto-grants-1997_08
Patent number
US05654323

Reaction notes

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