HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1280772Generated: October 30, 2026
Phthalimide → 2-(4-{1-[bis(4-Fluorophenyl)-methyl]-piperidin-4-yl}-butyl)-isoindol-1,3-dione
https://huagongshe.com/reaction/1280772
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Phthalimide | HCID 6809 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | ethyl N-ethoxycarbonyliminocarbamate | HCID 220568 | — |
| Reactant | 4-{1-[Bis(4-fluorophenyl)-methyl]-piperidin-4-yl}-butan-1-ol | HCID 18425711 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2-(4-{1-[bis(4-Fluorophenyl)-methyl]-piperidin-4-yl}-butyl)-isoindol-1,3-dione | HCID 18425717 | — |
Reaction Steps
23.1 g (62.5 mmol) 4-{1-[bis(4-fluorophenyl)-methyl]-piperidin-4-yl}-butan-1-ol, 16.4 g (62.5 mmol) triphenylphosphine and 9.2 g (62.5 mmol) phthalimide are suspended in THF and 10.9 g (62.5 mmol) azodicarboxylic acid diethyl ester is added dropwise under a protective atmosphere and light cooling (ca. 15-25° C.). The mixture is stirred for three hours at RT and subsequently the solvent is removed under vacuum. The residue is chromatographically purified over silica gel with CH2Cl2/CH3OH (99.5/0.5) Yield: 27.6 g (90%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06451816B1 |
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| Source dataset | uspto-grants-2002_09 |
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| ORD ID | ord-85a2ace78a804e8d96b06fd3042bbe09 |
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| Source note | uspto-grants-2002_09 |
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