Dimethylformamide → N-Methyl-N-(2-(3-chloro-4-methoxyphenyl)ethyl)-1,4-diaminobutane

HRID 373938노트

반응식

HRID 373938 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][NH2:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].Br[CH2:14][CH2:15][CH2:16][CH2:17][N:18]1C(=O)C2=CC=CC=C2C1=O.[C:29](=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:29][N:12]([CH2:11][CH2:10][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([Cl:1])[CH:3]=1)[CH2:14][CH2:15][CH2:16][CH2:17][NH2:18]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 93575N-(4-Bromobutyl)phthalimideHCID 27576442-(3-Chloro-4-methoxyphenyl)ethan-1-amine

생성물 1

HCID 19926614N-Methyl-N-(2-(3-chloro-4-methoxyphenyl)ethyl)-1,4-diaminobutane수율 47%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture comprising 5.00 g of N-methyl-(2-(3-chloro-4-methoxyphenyl)ethylamine, 9.49 g of N-(4-bromobutyl)phthalimide, 4.16 g of anhydrous potassium carbonate and 50 ml of N,N-dimethylformamide was stirred at a room temperature for 14 hours, followed by the addition of water. The obtained mixture was extracted with ethyl acetate and the ethyl acetate phase was washed with water and a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate and concentrated, followed by the addition of 50 ml of ethanol and 1.5 ml of hydrazine monohydrate. The obtained mixture was heated under reflux for 2 hours, cooled by allowing to stand and filtered to remove insoluble matter. The filtrate was distilled to obtain 3.16 g of the title compound as a colorless oil (yield: 47%).

후처리

  1. extractionThe obtained mixture was extracted with ethyl acetate
  2. washthe ethyl acetate phase was washed with water
  3. dry with materiala saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. additionfollowed by the addition of 50 ml of ethanol and 1.5 ml of hydrazine monohydrate
  6. temperatureThe obtained mixture was heated
  7. temperatureunder reflux for 2 hours
  8. temperaturecooled
  9. filtrationfiltered
  10. customto remove insoluble matter
  11. distillationThe filtrate was distilled

출처 및 근거

ORD 기록
ord-cdd354a3836647578dbf30cadcfed96b
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05166188

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