Water → HCID 18670631, compound

HRID 1059324Notes

Reaction equation

HRID 1059324 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29].[OH2:33]>CN(C)C=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[CH:22]=[CH:21][C:20]([O:33][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 12183Ethyl iodoacetateHCID 24758Sodium hydrideHCID 18670603HCID 18670603, compound

Product 1

HCID 18670631HCID 18670631, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.5 g of [1-(benzyloxycarbonyl)piperidin-4-yl]phenol in 20 ml of N,N-dimethylformamide was added 0.083 g of sodium hydride (60% or more oily) and the resulting mixture was stirred at room temperature for 10 minutes. Next, ethyl iodoacetate was added thereto and the resulting mixture was reacted at 60° C. for 1.5 hours. The reaction mixture was poured into water, extracted with ethyl acetate, washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 0.4 g of the title compound as a colorless oily substance.

Workup

  1. customthe resulting mixture was reacted at 60° C. for 1.5 hours
  2. extractionextracted with ethyl acetate
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter distilling off the solvent under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-893e186f062648d5b95ddee786f0cb92
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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