HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → (4-benzylpiperidin-1-yl)-(6-hydroxy-1H-indol-2-yl)methanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-Benzylpiperidine | HCID 31738 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | 6-Hydroxy-1H-indole-2-carboxylic acid | HCID 22350191 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (4-benzylpiperidin-1-yl)-(6-hydroxy-1H-indol-2-yl)methanone | HCID 9797767 | 71.6% |
Reaction Steps
A mixture of 5.0 g (28.2 mmol) of 6-hydroxy-indole-2-carboxylic acid [J. Chem. Soc. 1605-1608. (1948)], 4.4 ml (31.6 mmol) of triethylamine, 5.0 g (28.5 mmol) of 4-benzylpiperidine, 12.0 g (31.6 mmol) of HBTU (Advanced Chem. Tech.) and 50 ml of dimethylformamide is stirred at room temperature for 6 h. The precipitated product is filtered off and recrystallized from ethanol to yield 6.75 g (71%) of the title compound. Mp: 214-215° C. (ethanol).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06919355B2 |
| Source dataset | uspto-grants-2005_07 |
| ORD ID | ord-ca99504672fa409690096faf5f6866fb |
| Source note | uspto-grants-2005_07 |