Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Methylpiperazine | HCID 53167 | — |
| Reactant | Methyl 5-(bromomethyl)-2-nitrobenzoate | HCID 13399988 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 66671056 | HCID 66671056 | — |
Reaction Steps
To a solution of 5-bromomethyl-2-nitrobenzoic acid methyl ester (3.00 g, 10.9 mmol) in CH2Cl2 (100 mL) was added triethylamine (3.30 g, 33.0 mmol) and 1-methylpiperazine (3.30 g, 33.0 mmol). The mixture was heated at 50° C. under nitrogen for 16 hours, then concentrated to give crude 5-(4-methylpiperazin-1-ylmethyl)-2-nitrobenzoic acid methyl ester, which was purified by column chromatography (silica gel 230-400 mesh; 1-5% methanol in dichloromethane as eluent). Yield: 3.0 g (93%). It was further converted to its hydrochloride salt (3.7 g) by stirring in 1 M HCl in ether and was isolated by filtration.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09238640B2 |
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| Source dataset | uspto-grants-2016_01 |
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| ORD ID | ord-a6243f6d7d044514b84f3762d4d577a7 |
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| Source note | uspto-grants-2016_01 |
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