HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 4-Fluoro-N-[6-(1-methyl-piperidin-4-ylcarbonyl)-pyridin-2-yl]-benzamide dihydrochloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 4-Fluorobenzoyl chloride | HCID 67879 | — |
| Reactant | (6-Aminopyridin-2-yl)(1-methylpiperidin-4-yl)methanone | HCID 11401723 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 4-Fluoro-N-[6-(1-methyl-piperidin-4-ylcarbonyl)-pyridin-2-yl]-benzamide dihydrochloride | HCID 67441227 | — |
Reaction Steps
Stir a mixture of 2-Amino-6-(1-methylpiperidin-4-ylcarbonyl)pyridine (0.150 g), 4-fluorobenzoyl chloride (0.218 g), triethylamine (0.192 mL) and dichloromethane at room temperature for 4 hours. Add 1N aqueous NaOH to basify the reaction mixture. Extract the mixture with dichloromethane, dry the organic phase with anhydrous sodium sulfate, evaporate the solvent, and purify the residue by HPLC to provide the free base of the title compound. Re-dissolve the free base in diethyl ether and add excess 1 M HCl. Evaporate the solvent and dry the residue under vacuum to obtain 80 mg of the title compound. M.p. 75-80° C.; HRMS: 342.1605 (obs.) (Cal. 342.1618).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08044207B2 |
| Source dataset | uspto-grants-2011_10 |
| ORD ID | ord-5aa5bcb2cf9940bfa45cd5c7587572e8 |
| Source note | uspto-grants-2011_10 |