Chloroacetyl chloride → 2-chloro-N-(2-morpholin-4-ylethyl)acetamide

Temperature

5 °C

Chloroacetyl chloride (1.73 g, 15 mmol) was dissolved in 4 mL of dichloromethane and cooled to 5° C. in an ice-water bath. 4-(2-Aminoethyl)morpholine (2 g, 15 mmol) was dissolved in 4 mL of dichloromethane containing triethylamine (3.03 g, 30 mmol) which was then added to this cold solution at 5° C. A solid precipitate formed immediately after the triethylamine was added. The reaction mixture was stirred for 3 hours at room temperature. The reaction mixture was diluted with 100 mL of dichloromethane and 20 mL of water. The organic solution was washed with 5% aqueous NaHCO3 (2×50 mL), brine (1×50 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The resulting residue was dried in vacuo to give 2.57 g (83.7%) of N-(2-chloroacetyl)-2-(4-morpholinyl)ethylamine as a yellow solid. 1H NMR (300 MHz / CDCl3): ∂ 2.48-2.55 (m, 6H), 3.38 (dd, 2H, J=5.63 Hz), 3.71 (t, 4H, J=4.53 Hz), 4.04 (s, 2H); mass spectrum, m/z=207.1 (M+H); HRMS calcd for C8H15N2O2Cl1 206.0822, found 206.0814.

1. additionwas then added to this cold solution at 5° C
2. additionwas added
3. washThe organic solution was washed with 5% aqueous NaHCO3 (2×50 mL), brine (1×50 mL)
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe resulting residue was dried in vacuo

ORD record

ord-504bb4e7671c41a68ae7bc14392734fe

Source dataset

uspto-grants-1998_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05753660