تفاعل #2557

ord-237b1973c5eb44b6bba25ecc54bfc269

معادلة التفاعل

[BH3-]C#N.[Na+]
sodium cyanoborohydride
CCOC(CN1CCC(C(=O)c2ccc(F)cc2)CC1)OCC
1-(2,2-Diethoxyethyl)-4-(4-fluorobenzoyl)piperidine
Cl
hydrochloric acid
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
COc1ccccc1N
o-anisidine
COc1ccccc1NCCN1CCC(C(=O)c2ccc(F)cc2)CC1
title compound
المردود 66.2%
COc1ccccc1NCCN1CCC(C(=O)c2ccc(F)cc2)CC1
4-(4-Fluorobenzoyl)-1-[2-(2-methoxyanilino)ethyl]piperidine
المردود 66.2%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىat room temperature
  2. 2
    أخرىthe solvent was removed by evaporation
  3. 3
    workup.DISTILLATIONthe resulting residue was subjected to azeotropic distillation
  4. 4
    أخرىto obtain an orange glutinous material
  5. 5
    أخرىat room temperature
  6. 6
    workup.STIRRINGAfter 2 hours of stirring at the same temperature
  7. 7
    استخلاصextracted with ethyl acetate
  8. 8
    غسيلwashed with water and saturated brine
  9. 9
    تجفيفThe resulting organic layer was dried on anhydrous sodium carbonate
  10. 10
    أخرىthe solvent was removed by evaporation
  11. 11
    أخرىthe resulting residue was purified

الإجراء التجريبي

1-(2,2-Diethoxyethyl)-4-(4-fluorobenzoyl)piperidine (81 mg, 0.25 mmol) was dissolved in THF (3 ml) to which was subsequently added 10% hydrochloric acid (2 ml) at room temperature. After 1 hour of stirring at the same temperature, the solvent was removed by evaporation, and the resulting residue was subjected to azeotropic distillation using benzene (5 ml×4) to obtain an orange glutinous material. The thus obtained residue was dissolved in methanol (2 ml) to which were subsequently added o-anisidine (29 μl, 0.25 mmol) and sodium cyanoborohydride (11 mg, 0.166 mmol) at room temperature. After 2 hours of stirring at the same temperature, the reaction solution was mixed with saturated sodium carbonate aqueous solution (10 ml), extracted with ethyl acetate and then washed with water and saturated brine. 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 (ether:hexane=2:1-ether) to obtain 59 mg (66.2%) of the title compound in the form of colorless solid.

المصدر

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