Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Hydrazine hydrate (1:1) | HCID 24654 | — |
| Reactant | Butanoic acid, 4-chloro-4-oxo-, methyl ester | HCID 73888 | — |
| Reactant | 1-[(3,4-Dichlorophenyl)methyl]piperidin-4-amine | HCID 10978156 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 22288615 | HCID 22288615 | — |
Reaction Steps
A solution of 1-(3,4-dichlorobenzyl)-piperidin-4-ylamine (2.2 g; JP 59101483) and triethylamine (1.53 ml) in dichloromethane (100 ml) stirring at ambient temperature was treated with 3-chlorocarbonyl-propionic acid methyl ester (1.14 ml). After stirring for 16 hours, the reaction mixture was washed with brine, the organic layer was dried (MgSO4), and evaporated to leave a white solid. This solid was suspended in ethanol (100 ml), treated with hydrazine hydrate (5 ml) and the resulting mixture was stirred at reflux for 2 hours and then allowed to cool. Water (30 ml) was added to the reaction mixture and the ethanol was evaporated. The aqueous residue was then extracted into dichloromethane (6×50 ml), the combined organics were dried (MgSO4) and evaporated to give the subtitle compound as a white solid. (1.9 g)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06958350B2 |
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| Source dataset | uspto-grants-2005_10 |
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| ORD ID | ord-96072b447e6141c69ff9ebd4987a9b0c |
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| Source note | uspto-grants-2005_10 |
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