Chloroacetyl chloride → Morpholine, 4-(chloroacetyl)-

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence