HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzenemethanamine, 3,4-dichloro- → {2-[4-(3,4-Dichlorobenzylamino)-2-methylquinolin-8-yloxy]-ethyl}-carbamate tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzenemethanamine, 3,4-dichloro- | HCID 1608 | — |
| Reactant | [2-(4-Chloro-2-methylquinolin-8-yloxy)-ethyl]-carbamate tert-butyl ester | HCID 59474799 | — |
| Catalyst | Copper sulfate pentahydrate | HCID 24463 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | {2-[4-(3,4-Dichlorobenzylamino)-2-methylquinolin-8-yloxy]-ethyl}-carbamate tert-butyl ester | HCID 25217468 | 13% |
Reaction Steps
[2-(4-Chloro-2-methylquinolin-8-yloxy)-ethyl]-carbamate tert-butyl ester (1.30 g, 3.86 mmole), 3,4-dichlorobenzylamine (1.36 g, 7.72 mmole) and a catalytic effective amount of copper(II)sulphate pentahydrate in dimethylsulfoxide (0.2 mL) were stirred at 155° C. for 30 min in a microwave oven. The organic phases were washed with water and saturated NaCl solution, dried and the solvent was removed. The residue thus obtained was purified using silica gel chromatography, eluting with dichloromethane:water 90:10. Precipitation in ethyl acetate gave a brownish solid (230 mg, 13%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08420670B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-db73224190db4ce3aa61e008ea4ef7df |
| Source note | uspto-grants-2013_04 |