Reaction #1105

Reaction equation

HCl

magnesium

octyl bromide

THF

4-(4-oxocyclohexylamino)-3-methoxy-2-methylpyridine

THF

→

4-[(4-Hydroxy-4-n-octyl)cyclohexylamino]-3-methoxy-2-methylpyridine

Conditions

Workup

1. 1
   workup.DISTILLATIONThe THF is then distilled off in vacuo at room temperature
2. 2
   Extractionthe product is extracted from the solution which

Procedure

The Grignard solution is prepared from 0.73 g of magnesium and 6.0 g of octyl bromide in 50 ml of absolute THF. 2.8 g of 4-(4-oxocyclohexylamino)-3-methoxy-2-methylpyridine in 20 ml of THF are added dropwise to the solution. After 2 hours the mixture is acidified with 2N HCl. The THF is then distilled off in vacuo at room temperature and the product is extracted from the solution which is rendered alkaline with methylene chloride. Further working up takes place as in the previous working procedure.

Source