Toluene → 1-[2-(2-Amino-4,5-dichlorophenyl)-ethylamino]-3-[N-methyl-N-(6,7-dimethoxy-1,2,3,4-tetrahydronaphth-2-yl)-amino]-propane

HRID 1380872노트

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HRID 1380872 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[CH:4][C:3]=1[CH2:10][C:11]([NH:13][CH2:14][CH2:15][CH2:16][N:17]([CH3:32])[CH:18]1[CH2:27][CH2:26][C:25]2[C:20](=[CH:21][C:22]([O:30][CH3:31])=[C:23]([O:28][CH3:29])[CH:24]=2)[CH2:19]1)=O.C1(C)C=CC=CC=1>O1CCCC1>[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[CH:4][C:3]=1[CH2:10][CH2:11][NH:13][CH2:14][CH2:15][CH2:16][N:17]([CH3:32])[CH:18]1[CH2:27][CH2:26][C:25]2[C:20](=[CH:21][C:22]([O:30][CH3:31])=[C:23]([O:28][CH3:29])[CH:24]=2)[CH2:19]1

참가 물질

4

반응물 2

HCID 1140TolueneHCID 53641682HCID 53641682, 화합물

생성물 1

HCID 233245711-[2-(2-Amino-4,5-dichlorophenyl)-ethylamino]-3-[N-methyl-N-(6,7-dimethoxy-1,2,3,4-tetrahydronaphth-2-yl)-amino]-propane

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
80 °C

실험 절차

Next, 1-[2-(2-amino-4,5-dichlorophenyl)-1-oxo-ethylamino]-3-[N-methyl-N-(6,7-dimethoxy-1,2,3,4-tetrahydronaphth-2-yl)-amino]-propane (4.8 g, 0.01 mol) is dissolved in absolute tetrahydrofuran (100 ml) and mixed with boron trifluoride-diethyl ether complex (1.25 g, 1.1 ml). Then, a 10M toluene solution of borane-dimethylsulphide complex (1.6 ml) diluted with absolute tetrahydrofuran (20 ml) is added to the reaction mixture with stirring, under a nitrogen atmosphere and with heating to reflux temperature, and the resulting mixture is refluxed for a further 8 hours. The solvent is distilled off in vacuo, the residue is heated in 6M hydrochloric acid (100 ml) to 80° C. for one hour, cooled and extracted twice with ethyl acetate. The hydrochloric acid solution is then made alkaline with 50% sodium hydroxide solution while cooling with ice water and extracted several times with methylene chloride. The extract is dried over magnesium sulphate, concentrated by evaporation in vacuo and the residue is purified by column chromatography over alumina N (170 g) [activity II, eluant: methylene chloride and increasing amounts of ethanol (up to 5%). Yield: 1 g.

후처리

  1. additionmixed with boron trifluoride-diethyl ether complex (1.25 g, 1.1 ml)
  2. additionis added to the reaction mixture
  3. temperaturewith heating
  4. temperatureto reflux temperature
  5. temperaturethe resulting mixture is refluxed for a further 8 hours
  6. distillationThe solvent is distilled off in vacuo
  7. temperaturecooled
  8. extractionextracted twice with ethyl acetate
  9. temperaturewhile cooling with ice water
  10. extractionextracted several times with methylene chloride
  11. dry with materialThe extract is dried over magnesium sulphate
  12. concentrationconcentrated by evaporation in vacuo
  13. customthe residue is purified by column chromatography over alumina N (170 g) [activity II, eluant
  14. temperaturemethylene chloride and increasing amounts of ethanol (up to 5%)

출처 및 근거

ORD 기록
ord-8411fb30f2e14f35af0fee7c4e013081
출처 데이터셋
uspto-grants-1986_04
특허 번호
US04584293

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