Реакция #466579

Уравнение реакции

sodium hydroxide

N-(3,5-bis-trifluoromethyl-benzyl)-N-methyl-6-piperazin-1-yl-4-o-tolyl-nicotinamide

N-(3,5-Bis-trifluoromethyl-benzyl)-N-methyl-6-piperazin-1-yl-4-o-tolyl-nicotinamide

2-(2-chloroethoxy)-ethanol

potassium carbonate

→

title compound

Выход 64.4%

N-(3,5-Bis-trifluoromethyl-benzyl)-6-{4-[2-(2-hydroxy-ethoxy)-ethyl]-piperazin-1-yl}-N-methyl-4-o-tolyl-nicotinamide

Выход 64.4%

Растворители

acetonitrile

Условия реакции

Обработка

1. 1
   workup.ADDITIONwere added
2. 2
   ЭкстракцияExtraction with 3 60-ml portions of dichloromethane
3. 3
   Сушкаdrying with sodium sulfate and concentration
4. 4
   Другоеgave 528 mg of the crude product

Методика

A mixture of 400 mg (0.746 mmol) N-(3,5-bis-trifluoromethyl-benzyl)-N-methyl-6-piperazin-1-yl-4-o-tolyl-nicotinamide (Example 53), 0.18 ml (1.7 mmol) 2-(2-chloroethoxy)-ethanol and 0.189 g (1.35 mmol) potassium carbonate in 8 ml acetonitrile was stirred at 85° C. for 48 h. After cooling to room temperature 40 ml 1 N sodium hydroxide solution were added. Extraction with 3 60-ml portions of dichloromethane, drying with sodium sulfate and concentration gave 528 mg of the crude product. Flash column chromatography afforded 300 mg (64.4%) of the title compound as a light-brown solid.

Источник