Potassium Hydroxide → HCID 12043124, compound

HRID 1937664Notes

Reaction equation

HRID 1937664 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-ea51cd8863c14b759aa42772bdea0723
Source dataset
uspto-grants-2002_05
Patent number
US06395753B1

Reaction notes

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