Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | HCID 11106179 | HCID 11106179 | — |
| Reactant | 1-(2-Tert-butylphenyl)piperazine dihydrochloride | HCID 66751149 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 66792781 | HCID 66792781 | 25% |
Reaction Steps
A mixture of 1-(2-tert-butylphenyl)piperazine dihydrochloride obtained in Reference Example 1 (0.30 g, 1.03 mmol), 1-phenylproline obtained in Reference example 7 (0.21 g, 1.08 mmol), triethylamine (0.22 g, 2.16 mmol), EDCI (0.21 g, 1.08 mmol) and HOBt (0.17 g, 1.08 mmol) in acetonitrile (10 mL) was stirred at room temperature for 16 h. The reaction mixture was concentrated under reduced pressure and the resulting residue was partitioned between ethyl acetate and water, and the suspension of white precipitate in ethyl acetate was washed with 10% sodium hydrogen carbonate solution, water, saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate 90:10 to 30:70) to afford the title compound (0.10 g, 25%) as a light brown amorphous powder.
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-5b41d0cc601c42a99c1bdbad5f83c600 |
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| Source note | uspto-grants-2014_10 |
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