Cyclopentylamine → Ethyl 3-(cyclopentylamino)propanoate

Participants

Reaction Conditions

Reaction Steps

Cyclopentylamine (1.72 g, 17.5 mmol) and 3-chloro-propionic acid ethyl ester (2.4 g, 18 mmol) were combined neat and K2CO3 (2.4 g, 18 mmol) and a catalytic amount of tetrabutylammonium iodide (ca. 5 mg) was added. The mixture was heated at 80° C. overnight. The resulting mixture was then partitioned between water and DCM. The organic layer was dried (MgSO4) and concentrated to provide 2.68 g (83%) of the title compound. 1H-NMR (400 MHz, CDCl3:) δ ppm 4.13 (p, 2H, J=7.0 Hz), 3.07 (p, 1H, J=6.7 Hz), 2.81-2.94 (m, 4H), 2.51 (t, 1H, J=6.5 Hz), 2.44 (t, 1H, J=7.4 Hz), 1.29-1.88 (m, 6H), 1.25 (t, 3H, J=7.1 Hz)

Provenance & Evidence