Chloroacetyl chloride → Morpholine, 4-(chloroacetyl)-

Temperature

5 °C

To an ice cold solution of chloroacetyl chloride (1.29 g, 11 mmol) in 10 mL of methylene chloride was added morpholine (1 g, 11 mmol) in 10 mL of methylene chloride containing triethylamine (2.32 g, 23 mmol). The reaction mixture was stirred at 5° C. for 30 minutes then warmed to room temperature and stirred for 18 hours. After quenching with water (20 mL) at 5° C., additional methylene chloride (100 mL) was added. The organic layer was separated, washed with 1N HCl (1×50 mL), saturated aqueous NaHCO3 (1×50 mL), brine (1×50 mL), dried over MgSO4, filtered and concentrated at reduced pressure. The concentrated residue was dried in vacuo to give 0.52 g (28.8%) of 4-(2-chloroacetyl)morpholine as a brown oil. 1H NMR (300 MHz / CDCl3): δ 3.51-3.54 (m, 2H), 3.61-3.64 (m, 2H), 3.68-3.74 (m, 4H), 4.06 (s, 2H). HRMS: calcd for C6H10N1O2 Cl1 164.0478, found 164.0498.

1. temperaturethen warmed to room temperature
2. stirringstirred for 18 hours
3. customAfter quenching with water (20 mL) at 5° C.
4. additionadditional methylene chloride (100 mL) was added
5. customThe organic layer was separated
6. washwashed with 1N HCl (1×50 mL), saturated aqueous NaHCO3 (1×50 mL), brine (1×50 mL)
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated at reduced pressure
10. customThe concentrated residue was dried in vacuo

ORD record

ord-fe370b650870442ab298b4b642d4d109

Source dataset

uspto-grants-1998_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05753660