HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 5-Chloro-3-[1[3-(dimethylamino)benzoyl]-1,2,3,6-tetrahydro-4-pyridinyl]-1H-indole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 5-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole | HCID 3050532 | — |
| Reactant | 3-Dimethylaminobenzoyl chloride | HCID 7010342 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 5-Chloro-3-[1[3-(dimethylamino)benzoyl]-1,2,3,6-tetrahydro-4-pyridinyl]-1H-indole | HCID 18406839 | 95% |
Reaction Steps
A mixture of 5-chloro-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (0.53 g, 2.3 mmol) (Eur. J. Med. Chem., 1987, 22, 33-43) and 3-(dimethylamino)benzoyl chloride (0.5 g, 2.3 mmol) (Chem. Pharm. Bull., 1980, 28, 2045-2051) in tetrahydrofuran was stirred and treated with triethylamine (0.64 mL, 2 eq). The mixture was stirred for 2 h, treated with aqueous sodium bicarbonate (50 mL) and extracted with ethyl acetate. The organic phase was washed with brine and dried (Na2SO4) to give the title compound (0.83 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06476028B1 |
| Source dataset | uspto-grants-2002_11 |
| ORD ID | ord-343eeec250434045b0a93fe0ea4fc762 |
| Source note | uspto-grants-2002_11 |