Réaction #684964

ord-78c996df416f467f9625a954b68b0ce5

Équation de réaction

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
Rendement 15.8%
CCCCc1ccc(Cc2nccc3cc(OC)ccc23)cc1
1-(4-Butylbenzyl)-6-methoxyisoquinoline
Rendement 15.8%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Températureunder reflux for 1 hour 30 minutes
  2. 2
    TempératureThe mixture was cooled on ice
  3. 3
    Extractionextracted with ethyl acetate
  4. 4
    Séchagedried over anhydrous magnesium sulfate
  5. 5
    Concentrationconcentrated under reduced pressure
  6. 6
    AutreThe residue was purified by silica gel column chromatography

Mode opératoire

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).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07897387B2uspto-grants-2011_03