Reaction #307390

Reaction equation

piperidin-4-yl-carbamic acid tert-butyl ester

iodo-cyclopentane

K2CO3

iodocyclo-pentane

K2CO3

→

(1-Cyclopentyl-piperidin-4-yl)-carbamic acid tert-butyl ester

Solvents

acetonitrile

Conditions

Workup

1. 1
   workup.ADDITIONwere added to the solution
2. 2
   workup.STIRRINGThe solution was stirred at room temperature for several hours
3. 3
   FiltrationThe solution was filtered over a bed of dicalite
4. 4
   Otherthe filtrate was evaporated under reduced pressure
5. 5
   Otherto obtain 3 (6.70 g, 25 mmol, quantitative)

Procedure

This compound was synthesized from the commercially available piperidin-4-yl-carbamic acid tert-butyl ester (2) (5 g, 25 mmol, 1 equiv) which was dissolved in acetonitrile (150 mL), followed by the addition of iodo-cyclopentane (9.79 g, 50 mmol, 2 equiv) and K2CO3 (3.45 g, 25 mmol, 1 equiv). The solution was stirred at room temperature for 48 hours. Due to the incompleteness of the reaction, iodocyclo-pentane (1.70 g, 8.69 mmol, 0.35 equiv) and K2CO3 (1 g, 7.25 mmol, 0.29 equiv) were added to the solution. The solution was stirred at room temperature for several hours. The solution was filtered over a bed of dicalite and the filtrate was evaporated under reduced pressure to obtain 3 (6.70 g, 25 mmol, quantitative). LRMS (ES+): m/z 269.

Source