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

HRID 48189노트

반응식

HRID 48189 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-56d8d6fd0fec42b1b74cd2fa0c344eb9
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06703388B2

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