Potassium Iodide → HCID 11025076, compound

HRID 1289805Notes

Reaction equation

Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9](=[O:22])[C:10]([CH:18]2[CH2:21][CH2:20][CH2:19]2)([OH:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:4][CH2:3]1.Br[CH2:24][CH2:25][CH:26]=[C:27]([CH3:29])[CH3:28].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH3:28][C:27]([CH3:29])=[CH:26][CH2:25][CH2:24][N:2]1[CH2:3][CH2:4][CH:5]([NH:8][C:9](=[O:22])[C:10]([CH:18]2[CH2:19][CH2:20][CH2:21]2)([OH:17])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:6][CH2:7]1

Participants

Conditions

Temperature: 70 °C

Procedure

0.83 g of N-(piperidin-4-yl)-2-cyclobutyl-2-hydroxy-2-phenylacetamide hydrochloride, 0.42 g of 5-bromo-2-methyl-2-pentene, 42 mg of potassium iodide and 1.42 g of anhydrous potassium carbonate were suspended in 25 ml of anhydrous N,N-dimethylformamide, and this suspension was stirred at 70° C. for 3 hours. The reaction mixture was cooled to room temperature, mixed with water, and then extracted with diethyl ether. The organic layer was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=2/1 to 1/4) to obtain 449 mg of the title compound.

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionextracted with diethyl ether
washThe organic layer was washed with a saturated aqueous solution of sodium chloride
dry with materialdried over anhydrous magnesium sulfate
distillationAfter the solvent was distilled off under reduced pressure
customthe resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=2/1 to 1/4)

Sources & evidence

ORD record: ord-c51d5703845e4b738d4bbc60de8b4f69
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05750540

Reaction notes

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