Reaction #632022

Reaction equation

Diethylether

2-(1,4-Diaza-bicyclo[3.2.2]non-4-yl)-pyrimidin-5-ylamine

phenylacetyl chloride

HCl

phenylacetyl chloride

→

hydrochloride

N-[2-(1,4-Diaza-bicyclo[3.2.2]non-4-yl)-pyrimidin-5-yl]-2-phenyl-acetamide hydrochloric acid salt

Solvents

ethanol

ethanol

triethylamine

ethanol

Conditions

Workup

1. 1
   workup.STIRRINGstirring for 15 hours
2. 2
   OtherThe crude mixture was purified by silica gel chromatography

Procedure

2-(1,4-Diaza-bicyclo[3.2.2]non-4-yl)-pyrimidin-5-ylamine (0.877 g, 4.00 mmol) and ethanol (50 ml) was mixed with phenylacetyl chloride (0.742 g, 4.8 mmol) and was stirred for 15 hours at room-temperature, followed by addition of phenylacetyl chloride (74 mg, 0.48 mmol) and stirring for 15 hours. Diethylether (30 ml) was added. The mixture was made alkaline by adding triethylamine (20 ml). The crude mixture was purified by silica gel chromatography, using a 10:1+1% dichloromethane:methanol+aqueous ammonia mixture as eluent. The corresponding hydrochloride was prepared by solving the free base in ethanol (10 ml, 99%) followed by addition of HCl in ethanol (2 ml, 3 M). Yield 710 mg (47%). LC-ESI−HRMS of [M+H]+ shows 338.1976 Da. Calc. 338.198085 Da, dev. −1.4 ppm.

Source