Benzylamine → HCID 13520966, compound

To a stirred, cooled (0° C.) solution of 14 g (0.093 mol) of ethyl malonyl chloride in 50 mL of methylene chloride under nitrogen was added dropwise a solution of 10 g (0.093 mol) of benzylamine in 50 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 13 mL (0.093 mol) of triethylamine in 50 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 by placing it in the 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 a crude product which was purified by flash-chromatography (silica gel, 50% ethyl acetate/hexane eluent) to give 12.5 g (61% yield) of ethyl N-benzylmalonamide.

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
12. customgave a crude product which
13. customwas purified by flash-chromatography (silica gel, 50% ethyl acetate/hexane eluent)

ORD record

ord-120d1d70591949e48467e395c866599b

Source dataset

uspto-grants-1992_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05118681