Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Propylamine | HCID 7852 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | HCID 19906412 | HCID 19906412 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 19906401 | HCID 19906401 | 70% |
Reaction Steps
A mixture of methyl 4-[7-(2-carboxypropyl)naphth-1-ylmethyl]-3-methoxybenzoate (1.176 g), 4-dimethylaminopyridine (440 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (690 mg), propylamine (0.295 ml) and methylene chloride (20 ml) was stirred for 18 h. Ethyl acetate (100 ml) was added, the solution was washed (1N hydrochloric acid, brine) and dried (MgSO4). Evaporation and flash chromatography, eluting with 2:30:70 triethylamine:ethyl acetate:petroleum ether, gave a solid. Recrystallization from methylene chloride and hexane, followed by grinding to a powder and vacuum drying, afforded methyl 4-[7-[2-(propylcarbamoyl)propyl]naphth-1-ylmethyl]-3-methoxybenzoate (910 mg, 70%) as a colorless solid; mp 129.5°-130.0° C.; MS(CI), m/e=434(M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US05095038 |
|---|
| Source dataset | uspto-grants-1992_03 |
|---|
| ORD ID | ord-6a5f6dedb3e84889a4b00970aab78ce4 |
|---|
| Source note | uspto-grants-1992_03 |
|---|
