Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 1-Amino-3-(diethylamino)propan-2-ol | HCID 97749 | — |
| Reactant | 2-Chloro-1-methylpyridinium iodide | HCID 167069 | — |
| Reactant | 3-Methoxy-1-phenyl-1H-indole-2-carboxylic acid | HCID 13135988 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | Eproxindine | HCID 54965 | — |
Reaction Steps
15 g of 2-chloro-N-methyl-pyridinium iodide in 150 ml of methylene chloride and 14 ml of triethylamine are added to 13.3 g of N-phenyl-3-methoxyindole-2-carboxylic acid, dissolved in 100 ml of methylene chloride, and the mixture is stirred at room temperature for one hour. 7.5 g of 3-(N,N-diethylamino)-2-hydroxypropylamine are then added, and the mixture is stirred at room temperature for a further 3 hours. The reaction solution is added to water and the mixture is extracted with methylene chloride. The organic phase is washed with dilute sodium hydroxide solution and water, dried and evaporated. The resulting oily title compound is converted into its hydrochloride in a manner corresponding to that in Example 1. Melting point: 148°-150° C., yield: 12 g.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04924004 |
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| Source dataset | uspto-grants-1990_05 |
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| ORD ID | ord-abecff870c7843f3b27aa4a9029714a3 |
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| Source note | uspto-grants-1990_05 |
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