Reacción #684964

ord-78c996df416f467f9625a954b68b0ce5

Ecuación de reacción

O=P(Cl)(Cl)Cl
Phosphorus oxychloride
CCCCc1ccc(CC(=O)NCC(O)c2cccc(OC)c2)cc1
compound
CCCCc1ccc(CC(=O)NCC(O)c2cccc(OC)c2)cc1
N-[2-Hydroxy-2-(3-methoxyphenyl)ethyl]-2-(4-butylphenyl)-acetamide
O=C([O-])O.[Na+]
sodium hydrogencarbonate
CCCCc1ccc(Cc2nccc3cc(OC)ccc23)cc1
title compound
Rendimiento 15.8%
CCCCc1ccc(Cc2nccc3cc(OC)ccc23)cc1
1-(4-Butylbenzyl)-6-methoxyisoquinoline
Rendimiento 15.8%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturaunder reflux for 1 hour 30 minutes
  2. 2
    TemperaturaThe mixture was cooled on ice
  3. 3
    Extracciónextracted with ethyl acetate
  4. 4
    Secadodried over anhydrous magnesium sulfate
  5. 5
    Concentraciónconcentrated under reduced pressure
  6. 6
    OtroThe residue was purified by silica gel column chromatography

Procedimiento

Phosphorus oxychloride (1.6 ml) was added to a solution of the compound of Example B145 (600 mg, 1.7 mmol) in acetonitrile (15 ml), and the mixture was stirred under reflux for 1 hour 30 minutes. The mixture was cooled on ice, made alkaline with a 5% aqueous sodium hydrogencarbonate solution, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (82 mg).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07897387B2uspto-grants-2011_03