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

HRID 1078356

반응식

HRID 1078356 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0177ce9340bb4430bfbc5c730d0f9a69
출처 데이터셋
uspto-grants-1996_08
특허 번호
US05547967

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