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

HRID 373938ノート

反応式

HRID 373938 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-cdd354a3836647578dbf30cadcfed96b
出典データセット
uspto-grants-1992_11
特許番号
US05166188

反応ノート

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