Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 1-(Methoxycarbonyl)cyclopropane-1-carboxylic acid | HCID 13861823 | — |
| Reactant | 1-(2-Tert-butylphenyl)piperazine dihydrochloride | HCID 66751149 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 66750880 | HCID 66750880 | 82% |
Reaction Steps
A suspension of 1-(2-tert-butylphenyl)piperazine dihydrochloride (Reference Example 1, 0.500 g, 1.72 mmol), 1-(methoxycarbonyl)cyclopropanecarboxylic acid (0.297 g, 2.06 mmol), EDCI (0.395 g, 2.06 mmol), HOBt (0.278 g, 2.06 mmol) and triethylamine (719 μl, 5.16 mmol) in acetonitrile (10 mL) was stirred at room temperature for 16 h. The reaction mixture was poured into saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was washed with saturated sodium hydrogen carbonate solution and brine, dried over MgSO4, and the solvent was evaporated under reduced pressure to give the crude product. The product was purified by flash column chromatography (silica gel, n-hexane/ethyl acetate=90:10 to 65:35) to provide methyl 1-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}cyclopropanecarboxylate (0.485 g, 82%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08853215B2 |
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| Source dataset | uspto-grants-2014_10 |
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| ORD ID | ord-bbad7d05c5664890bbfafbc3692d0b7f |
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| Source note | uspto-grants-2014_10 |
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