Sodium Iodide → HCID 11858317, compound

HRID 1710765Notes

Reaction equation

HRID 1710765 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][CH:14]=[C:15]([CH2:17][N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][C:19]3=[O:24])[N:16]=2)=[CH:8][CH:7]=1.[CH3:25][CH:26]1[CH2:30][CH2:29][CH2:28][NH:27]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[CH3:25][CH:26]1[CH2:30][CH2:29][CH2:28][N:27]1[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][CH:14]=[C:15]([CH2:17][N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][C:19]3=[O:24])[N:16]=2)=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 130032-MethylpyrrolidineHCID 59457504HCID 59457504, compound

Product 1

HCID 11858317HCID 11858317, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-({2-[4-(3-chloropropoxy)phenyl]-1,3-oxazol-4-yl}methyl)piperidin-2-one i55 (0.564 g, 1.62 mmol, 1 eq) is reacted with 2-methylpyrrolidine (0.19 ml, 1.94 mmol, 1.2 eq) in the presence of potassium carbonate (0.45 g, 3.24 mmol, 2 eq) and a catalytic quantity of sodium iodide in refluxing acetonitrile (20 ml). After 45 h, the solvent is evaporated. The residue is then taken up in ethyl acetate and washed two times with an aqueous solution of sodium hydrogenocarbonate. The organic layer is dried over magnesium sulfate, filtered and concentrated under vacuum. Purification by chromatography over silicagel (eluent: dichloromethane/methanol/ammonia 95:4.5:0.5) affords 0.27 g of 1-[(2-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}-1,3-oxazol-4-yl)methyl]piperidin-2-one 122.

Workup

  1. customthe solvent is evaporated
  2. washwashed two times with an aqueous solution of sodium hydrogenocarbonate
  3. dry with materialThe organic layer is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customPurification by chromatography over silicagel (eluent: dichloromethane/methanol/ammonia 95:4.5:0.5)

Sources & evidence

ORD record
ord-f3917507cbfc428e8905402495f862c3
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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