Sodium Iodide → HCID 66817909, compound

HRID 1754940Notes

Reaction equation

[H-].[Na+].[Na+].[I-].[Br:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([C:13]([N:15]2[CH2:18][CH:17]([OH:19])[CH2:16]2)=[O:14])=[CH:8][C:7]=1[CH3:20].Cl[CH2:22][CH2:23][CH2:24][N:25]([CH3:27])[CH3:26]>C1(C)C=CC=CC=1.CCOC(C)=O>[Br:5][C:6]1[C:7]([CH3:20])=[CH:8][C:9]([C:13]([N:15]2[CH2:16][CH:17]([O:19][CH2:22][CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[CH2:18]2)=[O:14])=[CH:10][C:11]=1[CH3:12]

Participants

Conditions

Temperature: 110 °C

Procedure

NaH (110 mg, 2.75 mmol, 60% oily suspension) and NaI (274 mg, 1.83 mmol) were added to a solution of (4-bromo-3,5-dimethyl-phenyl)-(3-hydroxy-azetidin-1-yl)-methanone (130 mg, 0.458 mmol) and (3-chloro-propyl)-dimethyl-amine (289 mg, 1.83 mmol) in toluene (1.8 ml). The mixture was stirred at 110° C. for 15 hours. The reaction mixture was diluted with AcOEt, and the organic layer was then sequentially washed with a saturated aqueous NaHCO3 solution, water and a saturated aqueous NaCl solution. Further, the organic layer was dried over sodium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane/AcOEt) to give (4-bromo-3,5-dimethyl-phenyl)-[3-(3-dimethylamino-propoxy)-azetidin-1-yl]-methanone (46 mg, 27%).

Workup

washthe organic layer was then sequentially washed with a saturated aqueous NaHCO3 solution, water
dry with materialFurther, the organic layer was dried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (n-hexane/AcOEt)

Sources & evidence

ORD record: ord-cd5348bc2fd54775869db1a4d52be4e6
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169254B2

Reaction notes

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