Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Benzoyl chloride | HCID 7412 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-(Piperidin-1-yl)-5-(trifluoromethyl)aniline | HCID 694756 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 886827 | HCID 886827 | 86.7% |
Reaction Steps
Benzoyl chloride (50.0 μl, 0.430 mmol, commercially available product) and triethylamine (170 μl, 1.21 mmol) were sequentially added at 0° C. to a dichloromethane (3 ml) solution of 2-(1-piperidinyl)-5-(trifluoromethyl)aniline (102 mg, 0.417 mmol), obtained as described in Referential Example 1-2. The resulting mixture was warmed to room temperature and stirred for 18 hours. Water was added to the mixture, and the resulting mixture was extracted three times with ethyl acetate. The obtained organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20 g, hexane/ethyl acetate=10/1). Thus, N-[2-(1-piperidinyl)-5-(trifluoromethyl)phenyl]benzamide (GIF-0344) (126 mg, 86.7%) was yielded as a colorless solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07569536B2 |
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| Source dataset | uspto-grants-2009_08 |
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| ORD ID | ord-3987062814db4b1398d014c56d49c419 |
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| Source note | uspto-grants-2009_08 |
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