Sodium Iodide → HCID 54174460, compound

HRID 1919550Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[NH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.[I-].[Na+].Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]1[C:24](=[O:25])[C:23]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]2[C:21]1=[O:30]>C(O)C.CC(C)=O>[N:7]1([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]2[C:21](=[O:30])[C:22]3=[CH:29][CH:28]=[CH:27][CH:26]=[C:23]3[C:24]2=[O:25])[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

Conditions

Temperature: 50 °C

Procedure

Potassium carbonate (13.57 g, 98.20 mmol), pyrrolidine (4.47 ml, 54.01 mmol) and sodium iodide (7.359 g, 49.098 mmol) were added to ethanol/acetone (1:1) at room temperature and stirred for 1 hour. To the reaction mixture was slowly added N-(5-bromopentyl)phthalimide (2) (10.60 g, 49.10 mmol), and the resulting reaction mixture was refluxed at 50° C. for 24 hours. After the reaction was completed, the resulting white solid was filtered and the solvent was evaporated under reduced pressure. Afterwards, the obtained residue was extracted with a saturated 1N NaOH aqueous solution and dichloromethane three times. Then, the organic phase was dried with anhydrous magnesium sulfate and distilled under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent: dichloromethane:methnol:ammonia water=100:9:1) to give the target compound (3.27 g, 45%).

Workup

customthe resulting reaction mixture
filtrationthe resulting white solid was filtered
customthe solvent was evaporated under reduced pressure
extractionAfterwards, the obtained residue was extracted with a saturated 1N NaOH aqueous solution and dichloromethane three times
dry with materialThen, the organic phase was dried with anhydrous magnesium sulfate
distillationdistilled under reduced pressure

Sources & evidence

ORD record: ord-766da45feb85480d886a2e9555e11cd9
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08168646B2

Reaction notes

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