Diisopropylethylamine → HCID 23325339, compound

Participants

Reaction Steps

A mixture of 5.6 g (0.02 moles) of 2-(1-piperazinyl)-7-(4-pyridyl)[1,2,4]triazolo[1,5-a]pyrimidine (prepared as described in Example 47), 4.0 g (0.02 moles) of α-chloro-p-fluorobutyrophenone, 3.6 g (0.027 moles) of N,N-diisopropylethylamine and 100 ml of 2-propanol was heated at reflux for 16 hours with stirring. The reaction mixture was evaporated in vacuo to a solid. The solid was dissolved in 100 ml of water and extracted twice with 100 ml of chloroform. The extracts were combined, dried over magnesium sulfate, filtered and evaporated to a dark syrup. The syrup was dissolved in dichloromethane and passed through a pad of magnesium silicate, washing with methylene chloride. This filtrate was collected and set aside. Then acetone was passed through the pad and the acetone filtrate was collected and evaporated to a syrup. The syrup was dissolved in 15 ml of ethanol, 200 ml of ether was added, then hexane until cloudy. Evaporation by boiling caused crystallization. The crude product was collected and washed with ether. Recrystallization from ethanol gave 1.2 g of the desired product as yellow crystals, mp 133°-135° C.

Provenance & Evidence