Benzaldehyde → 1,2-Dimethyl-10-(3-benzylaminopropyl)-phenothiazine-5-oxide

HRID 2296725Notes

Reaction equation

HRID 2296725 reaction equation
[CH3:1][C:2]1[C:15]2[N:14]([CH2:16][CH2:17][CH2:18][NH2:19])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[S:7](=[O:20])[C:6]=2[CH:5]=[CH:4][C:3]=1[CH3:21].[CH:22](=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O>C1(C)C=CC=CC=1>[CH3:1][C:2]1[C:15]2[N:14]([CH2:16][CH2:17][CH2:18][NH:19][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[S:7](=[O:20])[C:6]=2[CH:5]=[CH:4][C:3]=1[CH3:21]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 962WaterHCID 98611441,2-Dimethyl-10-(3-aminopropyl)phenothiazine-5-oxide

Product 1

HCID 120521971,2-Dimethyl-10-(3-benzylaminopropyl)-phenothiazine-5-oxideYield 97.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1.5 g of 1,2-dimethyl-10-(3-aminopropyl)phenothiazine-5-oxide obtained in Example 8 and 580 mg of benzaldehyde in 60 ml of toluene was stirred under reflux for 2 hr while using a water separator. Then the mixture was cooled to room temperature and the solvent was evaporated under reduced pressure. After adding 60 ml of ethanol and sodium borohydride successively, the reaction mixture was stirred under ice cooling for 10 min. After adding water, the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. After evaporating the solvent under reduced pressure, the residue was washed with diethyl ether to give 1.9 g of the title compound.

Workup

  1. temperatureunder reflux for 2 hr
  2. customthe solvent was evaporated under reduced pressure
  3. additionAfter adding 60 ml of ethanol and sodium borohydride successively
  4. additionAfter adding water
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customAfter evaporating the solvent under reduced pressure
  9. washthe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-cf35a5ad75bc4e2eb73ff17ce0543d1d
Source dataset
uspto-grants-2002_12
Patent number
US06489336B2

Reaction notes

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