Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | 3-(Chloromethyl)benzoic acid | HCID 241752 | — |
| Reactant | HCID 66638605 | HCID 66638605 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 66638508 | HCID 66638508 | 93% |
Reaction Steps
2-Amino-5-(3-piperidin-1-yl-propoxy)-benzoic acid methyl ester (compound A) (1.1 g) produced by the above process was dissolved in anhydrous methylene chloride (12 ml). Pyridine (600 μl) and 3-(chloromethyl)benzoyl chloride (compound B) (600 μl) were added dropwise to the solution at 0° C., and the mixture was stirred at room temperature for one hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was then subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 2-(3-chloromethyl-benzoylamino)-5-(3-piperidin-1-yl-propoxy)-benzoic acid methyl ester (1.5 g, yield 93%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08134015B2 |
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| Source dataset | uspto-grants-2012_03 |
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| ORD ID | ord-659d9536bb1c4f97bc1b46ab573aaee6 |
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| Source note | uspto-grants-2012_03 |
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