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

HRID 2296725ノート

反応式

HRID 2296725 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-cf35a5ad75bc4e2eb73ff17ce0543d1d
出典データセット
uspto-grants-2002_12
特許番号
US06489336B2

反応ノート

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