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

HRID 1388738Notes

Reaction equation

HRID 1388738 reaction equation
[CH:1]([CH:3]=O)=[O:2].[CH:5]1[O:6][CH:7]=[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=12.[NH2:14][CH:15]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1)[CH3:16].O>C1C=CC=CC=1>[CH3:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][CH:15]([NH:14][CH2:3][CH:1]([C:7]2[O:6][C:5]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[CH:8]=2)[OH:2])[CH3:16])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1991161-(4-Methylphenyl)propane-2-amineHCID 867392622-Benzofuran glyoxal

Product 1

HCID 12816501N-[2-(4-methylphenyl)-1-methylethyl]-2-(2-benzofuranyl)-2-hydroxyethanamineYield 76.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2-benzofuran glyoxal (10.44 g) and 2-amino-3-(4-methylphenyl)propane (8.94 g) was refluxed in benzene using a Dean and Stark head until the theoretical amount of water had been removed. The solvent was evaporated, replaced with methanol and sodium borohydride (5 g) added. The methanol was evaporated, the residue partitioned between water and ether and the ether layer dried. Filtration and evaporation gave an oil which was chromatographed on Kieselgel 60. Elution with 2% methanol-chloroform gave N-[2-(4-methylphenyl)-1-methylethyl]-2-(2-benzofuranyl)-2-hydroxyethanamine (14 g).

Workup

  1. customhad been removed
  2. customThe solvent was evaporated
  3. additionadded
  4. customThe methanol was evaporated
  5. customthe residue partitioned between water and ether
  6. dry with materialthe ether layer dried
  7. filtrationFiltration and evaporation
  8. customgave an oil which
  9. customwas chromatographed on Kieselgel 60
  10. washElution with 2% methanol-chloroform

Sources & evidence

ORD record
ord-078fba410be44c1d9a179a69f3cf3cc0
Source dataset
uspto-grants-1984_02
Patent number
US04432993

Reaction notes

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