Sodium Iodide → HCID 11952153, compound

HRID 251454Notes

Reaction equation

HRID 251454 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][CH2:14][C:15]([CH3:18])([CH3:17])[N:16]=2)=[CH:8][CH:7]=1.[I-].[Na+].[Na].[CH3:22][CH:23]1[CH2:27][CH2:26][CH:25]([CH3:28])[NH:24]1>C(#N)C.C(OCC)(=O)C.O>[CH3:22][CH:23]1[CH2:27][CH2:26][CH:25]([CH3:28])[N:24]1[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][CH2:14][C:15]([CH3:18])([CH3:17])[N:16]=2)=[CH:8][CH:7]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 960342,5-DimethylpyrrolidineHCID 5360545SodiumHCID 11950718HCID 11950718, compound

Product 1

HCID 11952153HCID 11952153, compoundYield 41%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-[4-(3-chloropropoxy)phenyl]-4,4-dimethyl-4,5-dihydro-1,3-oxazole ax10 (500 mg, 1.87 mmol, 1 eq), sodium iodide (0.56 mg, 3.74 mmol, 2 eq), sodium hydrogenocarbonate (0.31 mg, 3.74 mmol, 2 eq) and 2,5-dimethylpyrrolidine (0.24 ml, 2.8 mmol, 1.5 eq) are stirred at reflux overnight in dry acetonitrile (10 ml). Water and ethyl acetate are added to the mixture and the layers are separated. The organic layer is dried with brine, sodium sulfate and evaporated under vacuum. Flash chromatography over silica with ethyl acetate as the eluent gives 0.253 g of 2-(4-{3-[2,5-dimethylpyrrolidin-1-yl]propoxy}phenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole 18 as a free base.

Workup

  1. customthe layers are separated
  2. dry with materialThe organic layer is dried with brine, sodium sulfate
  3. customevaporated under vacuum

Sources & evidence

ORD record
ord-dcdf18bc8f604d12984beae1831bef3d
Source dataset
uspto-grants-2011_01
Patent number
US07863450B2

Reaction notes

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