Octylamine → HCID 19895382, compound

To a stirred, cooled (0° C.) solution of 21.5 g (0.143 mol) of ethyl malonyl chloride in 250 mL of methylene chloride under nitrogen was added dropwise a solution of 18.47 g (0.143 mol) of n-octylamine in 100 mL of methylene chloride over a half-hour period. After the addition the reaction mixture was allowed to warm to room temperature and stir for 2 h. The reaction mixture was cooled to 0° C. and a solution of 20 mL (0.143 mol) of triethylamine in 100 mL of methylene chloride was added dropwise over 2 h. Additional methylene chloride was added to keep the slurry of salts stirring efficiently. After the addition the reaction mixture was kept cold in a freezer. After 12 h the reaction was allowed to warm to room temperature and was immediately washed with water three times to remove the salts. The organic layer was dried over magnesium sulfate and filtered. Removal of solvent gave 29.5 g (84% yield) of ethyl N-n-octylmalonamide as a pale yellow solid.

1. additionAfter the addition the reaction mixture
2. temperatureThe reaction mixture was cooled to 0° C.
3. stirringstirring efficiently
4. additionAfter the addition the reaction mixture
5. waitAfter 12 h the reaction was allowed
6. temperatureto warm to room temperature
7. washwas immediately washed with water three times
8. customto remove the salts
9. dry with materialThe organic layer was dried over magnesium sulfate
10. filtrationfiltered
11. customRemoval of solvent

ORD record

ord-046a67b1200c49479a7c2fe5b964efbe

Source dataset

uspto-grants-1992_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05118681