Chloroacetyl chloride → Morpholine, 4-(chloroacetyl)-

Temperature

0 °C

To a stirring mixture of morpholine (1.00 g) and triethylamine (1.6 mL) in EtOAc (10 mL) at 0° C. is added chloroacetyl chloride (1.83 mL) dropwise. The mixture is stirred at 0° C. for 35 min., diluted with 10% HCl (25 mL) and extracted with EtOAc (3×50 mL). The organic layer is dried over MgSO4, and the solvent removed. The residue is purified by SiO2 flash column chromatography (eluent 35% EtOAc/hexane) to afford 1.42 g (76%) of the title compound as a yellow liquid. Physical characteristics: 1H NMR (CDCl3) δ 3.54, 3.64, 3.72, 4.07; IR (liq.) 2859, 1654, 1463, 1438, 1302, 1270, 1251, 1233, 1115, 1069, 1040, 965, 790, 657, 604 cm−1; MS (ESI+) m/z 164 (M+H)+. Anal. Found: C, 43.66; H, 6.17; N, 8.58.

1. extractionextracted with EtOAc (3×50 mL)
2. dry with materialThe organic layer is dried over MgSO4
3. customthe solvent removed
4. customThe residue is purified by SiO2 flash column chromatography (eluent 35% EtOAc/hexane)

ORD record

ord-5a4eb73d7fd3479fa426394d311922ab

Source dataset

uspto-grants-2003_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06559145B2