Sodium hydride → 2-Dimethylsulphamoyl-7-fluoro-10-(3-(4-methylpiperazin-1-yl)propyl)phenothiazine

HRID 1659092Notes

Reaction equation

HRID 1659092 reaction equation
[CH3:1][N:2]([CH3:21])[S:3]([C:6]1[CH:19]=[CH:18][C:17]2[S:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([F:20])[CH:14]=3)[NH:9][C:8]=2[CH:7]=1)(=[O:5])=[O:4].[H-].[Na+].Cl[CH2:25][CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]1>CN(C)C=O>[CH3:1][N:2]([CH3:21])[S:3]([C:6]1[CH:19]=[CH:18][C:17]2[S:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([F:20])[CH:14]=3)[N:9]([CH2:25][CH2:26][CH2:27][N:28]3[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]3)[C:8]=2[CH:7]=1)(=[O:4])=[O:5]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 669061-(3-Chloropropyl)-4-methylpiperazineHCID 21527012N,N-dimethyl-7-fluoro-phenothiazine-2-sulphonamide

Product 1

HCID 215270132-Dimethylsulphamoyl-7-fluoro-10-(3-(4-methylpiperazin-1-yl)propyl)phenothiazineYield 75.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

12 grams of N,N-dimethyl-7-fluoro-phenothiazine-2-sulphonamide were dissolved in 50 milliliters of dry dimethylformamide, 1.9 grams of 50% sodium hydride in oil added and the mixture stirred for 1 hour. 7.2 grams of 1-(3-chloropropyl)-4-methylpiperazine were then added and the mixture heated for two hours on a steam bath. Then the mixture was poured onto crushed ice, the resulting mixture extracted with ether, the ether phase washed, dried over anhydrous magnesium sulphate and the ether evaporated. 13 grams of 2-dimethylsulphamoyl-7-fluoro-10-(3-(4-methylpiperazin-1-yl)propyl)phenothiazine was thus obtained as a yellow oil. The dimaleate was made from an ethanol solution of the base and melted at 166°-169° Centigrade.

Workup

  1. temperaturethe mixture heated for two hours on a steam bath
  2. additionThen the mixture was poured
  3. customonto crushed ice
  4. extractionthe resulting mixture extracted with ether
  5. washthe ether phase washed
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customthe ether evaporated

Sources & evidence

ORD record
ord-0d47f33e0502409cb18c6acaab985618
Source dataset
uspto-grants-1976_06
Patent number
US03966930

Reaction notes

Loading…