Water → N-[2-(4-methylphenyl)-1-methylethyl]-2-(2-benzofuranyl)-2-hydroxyethanamine

HRID 1388735Notes

Reaction equation

HRID 1388735 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH:10]([OH:13])[CH2:11][NH2:12].[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22](=O)[CH3:23])=[CH:17][CH:16]=1.O>C1C=CC=CC=1>[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH:22]([NH:12][CH2:11][CH:10]([C:2]2[O:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[CH:3]=2)[OH:13])[CH3:23])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1374281-(4-Methylphenyl)propan-2-oneHCID 128143572-Amino-1-(1-benzofuran-2-yl)ethan-1-ol

Product 1

HCID 12816501N-[2-(4-methylphenyl)-1-methylethyl]-2-(2-benzofuranyl)-2-hydroxyethanamine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2-(2-benzofuranyl)-2-hydroxy ethanamine (1.0 g) and 4-methylphenylacetone (0.76 g) in benzene (50 ml) was heated under reflux using a Dean and Stark head until the required amount of water had been collected. The solvent was evaporated, replaced with ethanol (50 ml) and the solution hydrogenated at atmospheric pressure over platinum oxide until the theoretical amount of hydrogen had been taken up. The reaction mixture was filtered through diatomaceous earth, the filtrate evaporated and the residue chromatographed on Kieselgel 60. Elution with 2% methanolchloroform gave N-[2-(4-methylphenyl)-1-methylethyl]-2-(2-benzofuranyl)-2-hydroxy ethanamine, as an 80:20 mixture of diastereoisomers, m.p. 92-98 (cyclohexane).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customhad been collected
  4. customThe solvent was evaporated
  5. filtrationThe reaction mixture was filtered through diatomaceous earth
  6. customthe filtrate evaporated
  7. customthe residue chromatographed on Kieselgel 60
  8. washElution with 2% methanolchloroform

Sources & evidence

ORD record
ord-3c34c2a25e0f4b7c8e7a90306531e404
Source dataset
uspto-grants-1984_02
Patent number
US04432993

Reaction notes

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