تفاعل #2553

ord-b2d3298a193f4e188fb14350c59014ca

معادلة التفاعل

O=C(c1ccc(F)cc1)C1CCNCC1
4-(4-fluorobenzoyl)piperidine
OCCBr
2-bromoethanol
O=C(c1ccc(F)cc1)C1CCN(CCO)CC1
title compound
المردود 78.0%
O=C(c1ccc(F)cc1)C1CCN(CCO)CC1
4-(4-Fluorobenzoyl)-1-(2-hydroxyethyl)piperidine
المردود 78.0%

الكواشف

لا شيء

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةAfter 1 hour of heating
  2. 2
    درجة الحرارةunder reflux
  3. 3
    أخرىtriethylamine was removed by evaporation
  4. 4
    workup.ADDITIONthe resulting residue was mixed with saturated sodium carbonate aqueous solution (40 ml)
  5. 5
    استخلاصextracted with ethyl acetate
  6. 6
    تجفيفThe resulting organic layer was dried on anhydrous sodium carbonate
  7. 7
    أخرىthe solvent was removed by evaporation
  8. 8
    أخرىthe resulting residue was purified

الإجراء التجريبي

In an atmosphere of argon, 4-(4-fluorobenzoyl)piperidine (2.07 g, 10 mmol) was dissolved in triethylamine (30 ml) to which was subsequently added dropwise 2-bromoethanol (1.1 ml, 14.7 mmol) at room temperature. After 1 hour of heating under reflux, triethylamine was removed by evaporation, and the resulting residue was mixed with saturated sodium carbonate aqueous solution (40 ml) and extracted with ethyl acetate. The resulting organic layer was dried on anhydrous sodium carbonate, the solvent was removed by evaporation and then the resulting residue was purified by subjecting it to a silica gel column chromatography (ethyl acetate-methylene chloride:methanol=10:1) to obtain 1.96 g (78.0%) of the title compound in the form of light yellow solid.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05728835uspto-grants-1998_03