Reaction #7007

Reaction equation

1-hydroxybenzotriazole hydrate

3-dimethylaminopropyl-3-ethylcarbodiimide hydrochloride

Butyric acid hydrazide

1-pyrimidin-2-yl-piperidine-4-carboxylic acid

→

title compound

Yield 62.0%

1-Pyrimidin-2-yl-piperidine-4-carboxylic acid N′-butyryl-hydrazide

Yield 62.0%

Solvents

dichloromethane

dichloromethane

sodium hydrogen carbonate

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   ConcentrationThe reaction mixture was concentrated under reduced pressure
3. 3
   Otherthe solid formed
4. 4
   Otherwas isolated by filtration
5. 5
   OtherThe material obtained
6. 6
   Otherwas dried under vacuum at 40° C.

Procedure

A mixture of 1-pyrimidin-2-yl-piperidine-4-carboxylic acid (3.0 g, 14.5 mmol)(see reference U.S. Pat. No. 4,826,843), 1-hydroxybenzotriazole hydrate (1.96 g, 14.5 mmol) and 1-(3-dimethylaminopropyl-3-ethylcarbodiimide hydrochloride (2.78 g, 14.5 mmol) in dichloromethane (100 ml) was stirred for 10 minutes. Butyric acid hydrazide (1.78 g, 17.4 mmol) was added and the reaction mixture was stirred under a nitrogen atmosphere for 18 hours. The reaction mixture was diluted with dichloromethane (100 ml) and sodium hydrogen carbonate solution was added. The reaction mixture was concentrated under reduced pressure and the solid formed was isolated by filtration. The material obtained was dried under vacuum at 40° C. to give the title compound (2.62 g).

Source