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

HRID 634756

反応式

HRID 634756 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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+)).

後処理

  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

出典と根拠

ORDレコード
ord-f099c0b95295424dbd47ac2862a6f7e0
出典データセット
uspto-grants-2001_02
特許番号
US06184236B2

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