Potassium Hydroxide → HCID 12043124, compound

HRID 395421Notes

Reaction equation

HRID 395421 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21]([C:25]3[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[C:27]([O:35][CH3:36])[CH:26]=3)[CH:20]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.[OH-].[K+]>CO>[CH3:32][O:31][C:29]1[CH:30]=[C:25]([C:21]2[CH:20]=[C:19]([CH2:18][O:17][CH:14]3[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]3)[CH:24]=[CH:23][N:22]=2)[CH:26]=[C:27]([O:35][CH3:36])[C:28]=1[O:33][CH3:34]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 22558016HCID 22558016, compound

Product 1

HCID 12043124HCID 12043124, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-(benzyloxycarbonyl)-4-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyloxy]piperidine (213 mg) in methanol (10 mL) was added 40% aqueous potassium hydroxide (10 mL). The mixture was stirred at 100° C. for 3 hours and evaporated. Water was added to the residue and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous sodium sulfate and evaporated. The residual oil was subjected to column chromatography of silica gel using chloroform-ammonia saturated methanol (20:1) to give the title compound.

Workup

  1. customevaporated
  2. additionWater was added to the residue
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-5c99dd972b724698a117b347a56c655e
Source dataset
uspto-grants-2003_08
Patent number
US06605620B1

Reaction notes

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