Triethylamine → N-(Cyclopropylmethyl)cyclopropanecarboxamide

Temperature

0 °C

Cyclopropyl carboxylic acid (1.0 g, 11.63 mmol) was added to a 50 mL two neck round bottom flask, along with DCM (25 mL). This mixture was cooled to 0° C., EDCI (4.15 g, 13.95 mmol) was added portionwise to the mixture with stirring under nitrogen atmosphere, and the temperature was maintained for 0.5 h. After this time, hydroxybenzotriazole (1.88 g, 13.95 mmol) was added to the 0° C. mixture which was stirred for 10 min, then triethylamine (1.7 g, 11.63 mmol) was added, and stirring of the mixture was continued at the same temperature for another 0.5 h. Then, cyclopropylmethylamine (0.825 g, 11.63 mmol) was added, and the reaction was allowed to reach RT, and stirring was continued overnight. The solvent was then removed in vacuo, and the crude residue was purified by passing through a column over 60-120 silica gel, eluting with dichloromethane, to afford the title compound (1.6 g), yield: 87%.

1. temperaturethe temperature was maintained for 0.5 h
2. stirringwas stirred for 10 min
3. stirringstirring of the mixture
4. customto reach RT
5. stirringstirring
6. waitwas continued overnight
7. customThe solvent was then removed in vacuo
8. customthe crude residue was purified
9. washeluting with dichloromethane

ORD record

ord-a0e4a9eec1fa47deb6b014783dcaf890

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09040558B2