Reaktion #220776

Reaktionsgleichung

4-(N-phenylcarbamoyl)benzyl chloride

4-[[N-(9-fluorenylmethyloxycarbonyl)glycyl]aminomethyl]piperidine

triethylamine

→

4-[(glycylamino)methyl]-1-[4-(N-phenylcarbamoyl)benzyl]piperidine

Ausbeute 30.2%

Lösungsmittel

acetonitrile

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred at 60° C. for another 5 hours
2. 2
   EinengenAfter concentrating
3. 3
   Sonstigethe obtained crude product
4. 4
   Sonstigewas purified by column chromatography (SiO2, 5% methanol/dichloromethane-triethylamine/methanol/dichloromethane=2:2:96)

Vorschrift

An acetonitrile (100 mL) solution of 4-(N-phenylcarbamoyl)benzyl chloride (800 mg, 3.26 mmol) was dropped into a mixture of 4-[[N-(9-fluorenylmethyloxycarbonyl)glycyl]aminomethyl]piperidine (1.27 g, 2.96 mmol) with triethylamine (1.25 mL, 8.88 mmol), KI (50 mg, 0.30 mmol) and acetonitrile (200 mL). The resulting mixture was stirred at room temperature for 19 hours and stirred at 60° C. for another 5 hours. After concentrating, the obtained crude product was purified by column chromatography (SiO2, 5% methanol/dichloromethane-triethylamine/methanol/dichloromethane=2:2:96) to provide 4-[(glycylamino)methyl]-1-[4-(N-phenylcarbamoyl)benzyl]piperidine (340 mg, 30%).

Quelle