Reaction #587683

Reaction equation

DCM

4-{[3-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)propyl]amino}-benzonitrile

K2CO3

1-chloropinacolone

→

title compound

Yield 75.4%

4-({3-[7-(3,3-Dimethyl-2-oxobutyl)-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl]propyl}amino)benzonitrile

Yield 75.4%

Solvents

MeCN

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   Filtrationthe mixture filtered
3. 3
   WashThe filter cake was then washed with a mixture of DCM and MeCN before the solvent
4. 4
   Otherwas evaporated from the filtrate
5. 5
   OtherThe resulting residue was purified by chromatography on silica
6. 6
   Washeluting with a gradient of ethyl acetate methanol

Procedure

A mixture of 4-{[3-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)propyl]amino}-benzonitrile (Preparation C, 5.73 g 0.02 mol), K2CO3 (11.05 g, 0.08 mol) in MeCN (300 mL) was treated with 1-chloropinacolone (4.44 g, 0.032 mol). The mixture was stirred at 50° C. overnight before DCM was added and the mixture filtered. The filter cake was then washed with a mixture of DCM and MeCN before the solvent was evaporated from the filtrate. The resulting residue was purified by chromatography on silica, eluting with a gradient of ethyl acetate methanol:ammoniacal methanol (95:5:0 to 95:0:5), to give the title compound (5.8 g, 73.9%).

Source