1-Bromo-3-chloropropane → N-(3-Chloropropyl)-3,4-dimethoxy-N-methylphenethylamine

HRID 1078356

反応式

HRID 1078356 の反応式
Br[CH2:2][CH2:3][CH2:4][Cl:5].C(=O)([O-])[O-].[K+].[K+].[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH2:22][CH2:23][NH:24][CH3:25])[CH:17]=[CH:18][C:19]=1[O:20][CH3:21]>CN(C)C=O>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH2:22][CH2:23][N:24]([CH2:2][CH2:3][CH2:4][Cl:5])[CH3:25])[CH:17]=[CH:18][C:19]=1[O:20][CH3:21]

参加物

5

反応物 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 77039N-Methylhomoveratrylamine

生成物 1

HCID 577693N-(3-Chloropropyl)-3,4-dimethoxy-N-methylphenethylamine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

29 ml of 1-bromo-3-chloropropane were dissolved in 300 ml of dimethylformamide and 24 g of potassium carbonate were added to the solution. A solution of 18 g N-[2-(3,4-dimethoxyphenyl)-ethyl]-N-methylamine in 50 ml of dimethylformamide were added to the reaction mixture with stirring, dropwise within 2 hours. Then the reaction mixture was stirred for another hour. Then the salts formed were filtered off. The filtrate was concentrated at a maximum bath temperature of 50° C. The residue was dissolved in 200 ml of 0.5 m citric acid solution and the solution was extracted to remove unreacted bromochloropropane with methyl-tert-butyl ether. The aqueous phase was then made slightly alkaline by adding sodium hydrogen carbonate and extracted several times with ethyl acetate. Then the combined ethyl acetate extracts were dried with magnesium sulfate and concentrated. 21 g of 3-[N-(2-(3,4-dimethoxyphenyl)-ethyl)-N-methylamino]-propyl chloride were obtained as the residue.

後処理

  1. stirringThen the reaction mixture was stirred for another hour
  2. customThen the salts formed
  3. filtrationwere filtered off
  4. concentrationThe filtrate was concentrated at a maximum bath temperature of 50° C
  5. dissolutionThe residue was dissolved in 200 ml of 0.5 m citric acid solution
  6. extractionthe solution was extracted
  7. customto remove unreacted bromochloropropane with methyl-tert-butyl ether
  8. additionby adding sodium hydrogen carbonate
  9. extractionextracted several times with ethyl acetate
  10. dry with materialThen the combined ethyl acetate extracts were dried with magnesium sulfate
  11. concentrationconcentrated

出典と根拠

ORDレコード
ord-0177ce9340bb4430bfbc5c730d0f9a69
出典データセット
uspto-grants-1996_08
特許番号
US05547967

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