tert-butyl N-(1-cyanopiperidin-4-yl)carbamate synthesis

Yield:-

Reaction Conditions:

with sodium hydrogencarbonate in dichloromethane at 0 - 20; for 3 h;

Steps:

72
To a solution of piperidin-4-ylcarbamic acid tert-butyl ester (10. Og, 49.9mmol) in DCM (130mL) was added a slurry of NaHC0₃ (12.6g, 149.8mmol) in water (30mL) and the resulting mixture was cooled to 0°C. A solution of cyanogen bromide (6.4g, 59.9mmol) in DCM (15mL) was added, dropwise, over 10 min then the mixture was warmed to r.t and stirred for 3 h. The reaction mixture was diluted with water, then the layers were separated. The aqueous phase was extracted with DCM, then the organic fractions were combined, washed with sat. NaHC0₃ solution, then brine, and dried (MgS0₄). Removal of the solvent in vacuo afforded the title compound: RT = 2.93 min; mlz (ES ) = 226.1 [M+ H]⁺.

References:

PROSIDION LIMITED;BARBA, Oscar;BELL, James, Charles;DUPREE, Tom, Banksia;FRY, Peter, Timothy;BERTRAM, Lisa, Sarah;FYFE, Matthew, Colin, Thor;GATTRELL, William;JEEVARATNAM, Revathy, Perpetua;KEILY, John;KRULLE, Thomas, Martin;MCDONALD, Russell, Walker;MORGAN, Trevor;RASAMISON, Chrystelle, Marie;SCHOFIELD, Karen, Lesley;STEWART, Alan, John, William;SWAIN, Simon, Andrew;WITHALL, David, Matthew WO2011/147951, 2011, A1 Location in patent:Page/Page column 57