HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Chlorobenzoic Acid → HCID 69379171, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Chlorobenzoic Acid | HCID 6318 | — |
| Reactant | 2-(5-Methoxy-2-methyl-1H-indol-3-yl)ethanamine | HCID 52899 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 69379171 | HCID 69379171 | — |
Reaction Steps
A reaction mixture containing Compound 7 oxalate salt (520 mg, 2.55 mmol), EDCl (489 mg, 2.55 mmol), DMAP (31 mg, 0.255 mmol), and 4-chlorobenzoic acid (354 mg, 2.26 mmol) in anhydrous methylene chloride (15 mL) was stirred at rt for 3 hours. The reaction mixture was diluted with water and extracted with CH2Cl2 (2×15 mL). The combined CH2Cl2 extracts were washed with water, dried (MgSO4), filtered, and the solvent concentrated in vacuo. The crude amide was chromatographed on silica gel (EtOAc:hexanes; 25:75 then 60:40) to afford the precursor amide Compound 8e as a yellow oil (390 mg, 45%), which was used in the next step without any further characterization owing to its unstable nature.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06306890B1 |
| Source dataset | uspto-grants-2001_10 |
| ORD ID | ord-efbf90e5a65b4d2195a96c2145daa490 |
| Source note | uspto-grants-2001_10 |