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

HRID 48189Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 48189
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 120521971,2-Dimethyl-10-(3-benzylaminopropyl)-phenothiazine-5-oxideAusbeute 97,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-56d8d6fd0fec42b1b74cd2fa0c344eb9
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06703388B2

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