Morpholine → Acryloylmorpholine

A solution of morpholine (8.7 g, 0.1 mole) and triethylamine (15.3 ml, 0.1 mole) in ethyl ether (100 ml) was cooled to +5° C. A solution of acryloyl chloride (9.0 g, 0.10 mole) in 25 ml of ethyl ether was added dropwise over a 30 minute period, resulting in the formation of a white solid. An additional 100 ml of ethyl ether was added and the reaction stirred for 72 hours at room temperature. The white solid was filtered and washed well with ethyl ether. The ethyl ether wash and filtrate were combined and solvent removed, leaving an orange oil which was transferred to a 50 ml Erlenmeyer flask and dried overnight under nitrogen to yield 11.5 g of product. The structure was confirmed by NMR.

1. customresulting in the formation of a white solid
2. filtrationThe white solid was filtered
3. washwashed well with ethyl ether
4. washThe ethyl ether wash
5. customsolvent removed
6. customleaving an orange oil which
7. customdried overnight under nitrogen

ORD record

ord-689cdc64b5f44d938f8adf18839cf68b

Source dataset

uspto-grants-1991_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04981853