HuagongsheHuagongshe Chemistry Print Report · For research reference only
Imidazole → Tert-butyl 4-(3-iodopropyl)piperidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Imidazole | HCID 795 | — |
| Reactant | Iodine | HCID 807 | — |
| Reactant | Chlorodiphenylphosphine | HCID 66180 | — |
| Reactant | tert-Butyl 4-(3-hydroxypropyl)tetrahydro-1(2h)-pyridinecarboxylate | HCID 2800739 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | Tert-butyl 4-(3-iodopropyl)piperidine-1-carboxylate | HCID 9975355 | — |
Reaction Steps
To a stirred mixture of 3-3 (22.7 g, 93 mmol), chlorodiphenylphosphine (21.7 mL, 0.12 mol), imidazole (19.0 g, 0.28 mol), and toluene (300 mL) at 0° C. was added iodine (30.6 g, 0.12 mol) in toluene (700 mL) followed by removal of the cooling bath. After 2.0 h the reaction mixture was washed with saturated Na2CO3, 5% Na2S2O3, 10% KHSO4 and brine, dried (MgSO4), and concentrated. Flash chromatography (silica, 30% EtOAc/hexanes) gave 3-4 as a colorless oil, RF 0.41 (silica, 10% EtOAc/hexanes.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05786373 |
| Source dataset | uspto-grants-1998_07 |
| ORD ID | ord-5b9c470125314a8dbb696ffe62d5d590 |
| Source note | uspto-grants-1998_07 |