Chloroacetyl chloride → Benzyl 4-(2-chloroacetyl)morpholine-2-carboxylate

In a 100-mL round-bottom flask, the benzyl morpholine-2-carboxylate (50%, 1.00 g, 2.3 mmol) as the crude tfa salt was taken up in dichloromethane (8 mL), resulting in a white suspension. N-Ethyl-N-isopropylpropan-2-amine (1.4 ml, 7.9 mmol) was added, and the solid dissolved. The solution was cooled to 0 deg, and 2-chloroacetyl chloride (0.20 ml, 2.5 mmol) was added. The reaction mixture was allowed to warm naturally to ambient temperature where it was stirred for 14 h. The reaction mixture was diluted with DCM (75 mL), and the organic layer was extracted with dilute sodium bicarbonate (2×7 mL) then with half-saturated brine (7 mL), then was dried over sodium sulfate. The residue was purified through silica gel (100 mL) which had been deactivated with TEA (10 mL) using 90% EtOAc-hexane, affording the title compound (474 mg, 1.6 mmol). MS m/z 298 (M+1).

1. customresulting in a white suspension
2. dissolutionthe solid dissolved
3. temperatureThe solution was cooled to 0 deg
4. extractionthe organic layer was extracted with dilute sodium bicarbonate (2×7 mL)
5. dry with materialwith half-saturated brine (7 mL), then was dried over sodium sulfate
6. customThe residue was purified through silica gel (100 mL) which

ORD record

ord-3d4b83b1dfc54bf6a87d1301ca3eda95

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08163766B2