Phenethylamine → (1RS,2RS)-[2-(4-methoxy-phenyl)-cyclohexyl]-phenethyl-amine

HRID 634756

반응식

HRID 634756 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]2=O)=[CH:5][CH:4]=1.[CH2:16]([NH2:24])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]2[NH:24][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:5][CH:4]=1

참가 물질

5

반응물 3

HCID 1001PhenethylamineHCID 6101p-Toluenesulfonic acidHCID 2542922-(4-Methoxyphenyl)cyclohexanone

생성물 1

HCID 21260463(1RS,2RS)-[2-(4-methoxy-phenyl)-cyclohexyl]-phenethyl-amine

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of 2-(4-methoxyphenyl)-cyclohexanone (prepared following the procedure described in W. E. Bachmann et al., J. Am. Chem. Soc., 1950, 72, 1995) (2.0 g, 9.79 mmol), phenethylamine (1.19 g, 9.79 mmol), toluene (40 ml) and a catalytical amount of p-toluenesulfonic acid was refluxed in a Dean-Stark apparatus overnight. After removal of the solvent, the residue was dissolved in MeOH (25 ml) and sodium borohydride (excess) was added. After stirring for 1 h at RT, the solvent was evaporated, H2O was added to the residue. Extraction with CH2Cl2, drying of the organic layer over Na2SO4, evaporation of the solvent and chromatography of the residue over SiO2 (Merck 230-400 mesh) eluting with AcOEt gave (1RS,2RS)-[2-(4-methoxy-phenyl)-cyclohexyl]-phenethyl-amine (1.5 g, 50%, light yellow oil, MS: m/e=310.2 (M+H+)) and (1RS,2SR)-[2-(4-methoxy-phenyl)-cyclohexyl]-phenethyl-amine (0.95 g, 31%, light yellow oil, MS: m/e=310.2 (M+H+)).

후처리

  1. customprepared
  2. customAfter removal of the solvent
  3. dissolutionthe residue was dissolved in MeOH (25 ml)
  4. additionsodium borohydride (excess) was added
  5. customthe solvent was evaporated
  6. additionH2O was added to the residue
  7. extractionExtraction with CH2Cl2
  8. dry with materialdrying of the organic layer over Na2SO4, evaporation of the solvent and chromatography of the residue over SiO2 (Merck 230-400 mesh)
  9. washeluting with AcOEt

출처 및 근거

ORD 기록
ord-f099c0b95295424dbd47ac2862a6f7e0
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06184236B2

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