4-(2-Bromoethyl)phenol → 2,2-diphenyl-5-[N-(4-hydroxyphenethyl)-N-methylamino]pentanamide

HRID 1463856Notes

Reaction equation

HRID 1463856 reaction equation
[C:1]1([C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH2:11][CH2:12][CH2:13][NH:14][CH3:15])[C:8]([NH2:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:22][C:23]1[CH:31]=[CH:30][C:26]([CH2:27][CH2:28]Br)=[CH:25][CH:24]=1.C(=O)(O)[O-].[Na+]>C(#N)C>[C:1]1([C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH2:11][CH2:12][CH2:13][N:14]([CH2:28][CH2:27][C:26]2[CH:30]=[CH:31][C:23]([OH:22])=[CH:24][CH:25]=2)[CH3:15])[C:8]([NH2:10])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 842214-(2-Bromoethyl)phenolHCID 516892Sodium BicarbonateHCID 190884752,2-Diphenyl-5-methylaminopentanamide

Product 1

HCID 190885132,2-diphenyl-5-[N-(4-hydroxyphenethyl)-N-methylamino]pentanamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture containing 2,2-diphenyl-5-methylaminopentanamide (0.36 g--see Preparation 3), 4-hydroxyphenethyl bromide (0.26 g), sodium bicarbonate (0.5 g) and acetonitrile (20 ml) was heated under reflux for 16 hours. The mixture was partitioned between dichloromethane (40 ml) and aqueous sodium bicarbonate (30 ml), the layers separated and the aqueous layer extracted with dichloromethane (2×30 ml). The combined dichloromethane extracts were concentrated in vacuo to give an oil which was purified by column chromatography on silica eluting with dichloromethane containing methanol (0% up to 10%). The product-containing fractions were combined and concentrated in vacuo to give a foam which was further purified by column chromatography on alumina eluting with dichloromethane containing methanol (0% up to 10%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a foam, yield 0.09 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. customThe mixture was partitioned between dichloromethane (40 ml) and aqueous sodium bicarbonate (30 ml)
  4. customthe layers separated
  5. extractionthe aqueous layer extracted with dichloromethane (2×30 ml)
  6. concentrationThe combined dichloromethane extracts were concentrated in vacuo
  7. customto give an oil which
  8. customwas purified by column chromatography on silica eluting with dichloromethane
  9. additioncontaining methanol (0% up to 10%)
  10. concentrationconcentrated in vacuo
  11. customto give a foam which
  12. customwas further purified by column chromatography on alumina eluting with dichloromethane
  13. additioncontaining methanol (0% up to 10%)
  14. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-53d9bc1f31eb42ee8886a753ae1c574b
Source dataset
uspto-grants-1994_04
Patent number
US05302595

Reaction notes

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