Reaktion #694169

Reaktionsgleichung

cis-N-(6-benzhydryl-tetrahydropyran-3-yl)-amine

triethylamine

4-fluorophenylacetic acid

oxalyl chloride

→

cis-N-(6-benzhydryl-tetrahydropyran-3-yl)-2-(4-fluorophenyl)-acetamide

Ausbeute 80.0%

Cis-N-(6-benzhydryl-tetrahydro-pyran-3-yl)-2-(4-fluoro-phenyl)-acetamide

Ausbeute 80.0%

Lösungsmittel

dichloromethane

dichloromethane

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was removed in vacuo
2. 2
   workup.DISSOLUTIONthe residue was dissolved in dichloromethane (5 ml)
3. 3
   workup.WAITAfter 20 minutes the reaction mixture was allowed
4. 4
   Sonstigeto come to room temperature
5. 5
   workup.WAITAfter 3 hours
6. 6
   Waschenthe mixture was washed in turn with 1N NaHCO3, H2O and brine
7. 7
   Trocknendried over anhydrous Na2SO4
8. 8
   SonstigeThe solvent was removed in vacuo
9. 9
   Sonstigethe residue was purified by flash chromatography (hexane/ethyl acetate 7:3)

Vorschrift

Into a solution of 4-fluorophenylacetic acid (0.23 g, 1.46 mmol) in dichloromethane (25 ml) was added oxalyl chloride (0.22 g, 1.76 mmol) dissolved in dichloromethane (5 ml) at 0° C. which was followed by addition of one drop of DMF. The reaction mixture was allowed to reach at room temperature over a period of 2 hours. The solvent was removed in vacuo, and the residue was dissolved in dichloromethane (5 ml) and was added into a solution of cis-N-(6-benzhydryl-tetrahydropyran-3-yl)-amine (0.26 g, 0.96 mmol) and triethylamine (0.31 g, 1.46 mmol) in dichloromethane (25 ml) at 0° C. After 20 minutes the reaction mixture was allowed to come to room temperature. After 3 hours, more dichloromethane was added and the mixture was washed in turn with 1N NaHCO3, H2O and brine, then dried over anhydrous Na2SO4. The solvent was removed in vacuo, and the residue was purified by flash chromatography (hexane/ethyl acetate 7:3) to give cis-N-(6-benzhydryl-tetrahydropyran-3-yl)-2-(4-fluorophenyl)-acetamide 17 (0.31 g, yield 80%) as an oil.

Quelle