Reaction #7014

Reaction equation

chloroacetyl chloride

4-Hydrazinocarbonyl-piperidine-1-carboxylic acid tert-butyl ester

4-methylmorpholine

→

title compound

4-[N′-(2-Chloro-acetyl)-hydrazinocarbonyl]-piperidine-1-carboxylic acid tert-butyl ester

Solvents

dichloromethane

Conditions

Workup

1. 1
   TemperatureThe mixture was cooled
2. 2
   OtherThe reaction mixture was partitioned with aqueous sodium hydrogen carbonate solution
3. 3
   Dryingdried over magnesium sulphate
4. 4
   Filtrationfiltered
5. 5
   Otherthe filtrate evaporated

Procedure

4-Hydrazinocarbonyl-piperidine-1-carboxylic acid tert-butyl ester (see reference WO 9703986 A1 19970206)(25 g, 103 mmol) was dissolved in dichloromethane (300 ml) and 4-methylmorpholine (12.5 ml, 113 mmol) was added. The mixture was cooled using an ice bath and chloroacetyl chloride (8.2 ml, 103 mmol) was added drop wise. The reaction was warmed to room temperature and was stirred for 4 hours. The reaction mixture was partitioned with aqueous sodium hydrogen carbonate solution, dried over magnesium sulphate, filtered and the filtrate evaporated to give the title compound as an off white solid (29.6 g).

Source