Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Reactant | Dimethylazanium;chloride | HCID 12954980 | — |
| Reactant | HCID 18348660 | HCID 18348660 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 18348591 | HCID 18348591 | 96% |
Reaction Steps
A THF (16 ml) suspension of 4-[4-(4,5,6,7-tetramethoxyindan-1-yl)butoxy]benzoic acid (400 mg, 0.929 mmols), dimethylammonium chloride (150 mg, 1.86 mmols), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (357 mg, 1.86 mmols), 1-hydroxybenzotriazole monohydrate (285 mg, 1.86 mmols) and triethylamine (0.777 ml, 5.57 mmols) was stirred at room temperature for 12 hours. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and then dried. The solvent was evaporated out in vacuo, and the resulting crude product was purified by alumina column chromatography (ethyl acetate) followed by recrystallization (from hexane-ethyl acetate) to obtain the entitled compound (408 mg) as crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06326369B1 |
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| Source dataset | uspto-grants-2001_12 |
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| ORD ID | ord-795d4e0fc2d64b37834a39405f07844b |
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| Source note | uspto-grants-2001_12 |
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