Propanal → 4-(Prop-1-en-1-yl)morpholine

Temperature

-5 °C

A 500 ml 4-neck flask was equipped with a stirrer, thermometer, addition funnel and condenser. To the flask was charged 191.7 g (2.2 m) of morpholine and 138.2 g (1 m) of potassium carbonate (anhydrous) and the mixture was stirred and cooled to -5° C. with an ice-salt bath. To the flask was added 58 g (1 m) of propionaldehyde over a period of 55 minutes at a pot temperature of -5° C. The temperature was then allowed to rise to 25° to 27° C. and the reaction was continued for 2 hours at 25° C. The product was filtered and the filter cake washed with four 15 ml washes of toluene. The fitrate was heated under vacuum while morpholine was stripped using a 1 foot Vigreux column. This treatment was carried out at an oil bath temperature of 85° to 112° C., a pot temperature of 70° to 90° C., a vapor temperature of 41° to 58° C. and at a pressure of approximately 35 to 40 mm of Hg. The vacuum stripping was carried out until 133.3 g of product was obtained as a residue. GLC and GC/MS established that the predominant product was 4-(2-propenyl)morpholine. 13C NMR in d6 -DMSO (in δ units): 15.2 (CH3); 95.1 (CH3 --CH)=; 140.8 (--CH=CH--); 49.4 (--N(--CH2 --)2); and 66.1 (O(--CH2 --)2).

1. customA 500 ml 4-neck flask was equipped with a stirrer
2. additionthermometer, addition funnel and condenser
3. customto rise to 25° to 27° C.
4. filtrationThe product was filtered
5. washthe filter cake washed with four 15 ml
6. temperatureThe fitrate was heated under vacuum while morpholine
7. customThis treatment was carried out at an oil bath
8. customtemperature of 85° to 112° C.
9. customa pot temperature of 70° to 90° C.
10. customa vapor temperature of 41° to 58° C.
11. customwas obtained as a residue

ORD record

ord-33bb59becf104684a1b21b5c19697b00

Source dataset

uspto-grants-1987_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04687854