Phenethylamine → HCID 21260532, compound

HRID 634763Notes

Reaction equation

HRID 634763 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:14][CH2:13][CH2:12][C:11](=O)[CH:10]=2)=[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]([C:9]2[CH2:14][CH2:13][CH2:12][CH:11]([NH:24][CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:10]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 6101p-Toluenesulfonic acidHCID 3679273-(4-Methoxyphenyl)-2-cyclohexen-1-one

Product 1

HCID 21260532HCID 21260532, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-(4-methoxy-phenyl)-cyclohex-2-enone (prepared following the procedure described in CA:54-10947d) (2.0 g, 9.89 mmol), phenethylamine (1.20 g, 9.89 mmol), toluene (50 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 (30 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 flash-chromatography of the residue over SiO2 (Biotage-40, 90 g) eluting with CH2Cl2—MeOH 95:5 gave (RS)-[3-(4-methoxy-phenyl)-cyclohex-2-enyl]-phenethyl-amine (1.7 g, 56%, light yellow solid, MS: m/e=308.2 (M+H+)).

Workup

  1. customprepared
  2. customAfter removal of the solvent
  3. dissolutionthe residue was dissolved in MeOH (30 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 flash-chromatography of the residue over SiO2 (Biotage-40, 90 g)
  9. washeluting with CH2Cl2—MeOH 95:5

Sources & evidence

ORD record
ord-d2e0f96176904d28acab177ad32fff40
Source dataset
uspto-grants-2001_02
Patent number
US06184236B2

Reaction notes

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