HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → HCID 71138476, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Dimethylamine, hydrochloride | HCID 10473 | — |
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | 1-(3-Bromophenyl)piperidine-4-carboxylic acid | HCID 69570883 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 71138476 | HCID 71138476 | 101% |
Reaction Steps
To a solution of 1-(3-bromophenyl)piperidine-4-carboxylic acid (2 g, 7.0 mmol) in dioxane (70 mL), was added thionyl chloride (2.6 mL, 35 mmol) at 0° C. The mixture was kept at rt for 1 h and evaporated. The residue was co-evaporated with dichloromethane and dissolved in dichloromethane (5 mL). To this mixture, were added the mixture of dimethylamine HCl salt (1.7 g, 21 mmol), triethylamine (4.9 mL, 35 mmol) and dichloromethane (20 mL) at 0° C. The mixture was stirred at rt for 1 h and diluted with water and separated. The organic phase was dried and evaporated. The residue was purified with silica gel column chromatography (hexane/ethyl acetate 10:0 to 1:9) to give the titled compound (2.2 g, 100%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08962619B2 |
| Source dataset | uspto-grants-2015_02 |
| ORD ID | ord-bea6faba3dac4ee0a95bcb2cf4a19745 |
| Source note | uspto-grants-2015_02 |