Potassium Carbonate → tert-Butyl (1-cyclopentylpiperidin-4-yl)carbamate

Reaction equation

[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].I[CH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

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.