HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 10169Generated: October 26, 2026
Dimethylformamide → (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)-4-[3-(2-methyl-1,3-dioxolan-2-yl)propyl]piperazine
https://huagongshe.com/reaction/10169
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 2-(3-Chloropropyl)-2-methyl-1,3-dioxolane | HCID 80079 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)piperazine | HCID 10972505 | — |
| Solvent | Water | HCID 962 | — |
| Product | (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)-4-[3-(2-methyl-1,3-dioxolan-2-yl)propyl]piperazine | HCID 58681859 | 40% |
Reaction Steps
A mixture of 5-chloro-2-pentanone ethylene ketal (0.54 g), (2R)-1-[3,5-bis(trifluoro-methyl)benzoyl]-2-(1H-indol-3-ylmethyl)piperazine (1.37 g), diisopropylethylamine (0.6 mL), and dimethylformamide (25 mL) was heated overnight, at 90°C. After cooling to room temperature the mixture was poured in water and extracted with ethyl acetate. The organic layer was dried (Na2SO4), and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, CH2Cl2/MeOH 95/15) to afford (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)-4-[3-(2-methyl-1,3-dioxolan-2-yl)propyl]piperazine (0.7 g, 40%). MH+ 584.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07094779B2 |
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| Source dataset | uspto-grants-2006_08 |
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| ORD ID | ord-01898ff63c1d4a31a48358210ecd48cd |
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| Source note | uspto-grants-2006_08 |
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