Sodium Hydroxide → 4-[N-methyl-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]piperidine

HRID 2300347Notes

Reaction equation

HRID 2300347 reaction equation
C(OC([N:6]1[CH2:11][CH2:10][CH:9]([N:12]([CH3:32])[CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[C:16]([C:20]3[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=3)[CH:15]=2)[CH2:8][CH2:7]1)=O)C.[OH-].[Na+]>C(O)C>[CH3:32][N:12]([CH:9]1[CH2:10][CH2:11][NH:6][CH2:7][CH2:8]1)[CH2:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([C:20]2[CH:21]=[C:22]([O:30][CH3:31])[C:23]([O:28][CH3:29])=[C:24]([O:26][CH3:27])[CH:25]=2)[CH:15]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 225580131-(ethoxycarbonyl)-4-[N-methyl-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]piperidine

Product 1

HCID 225578634-[N-methyl-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]piperidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-(ethoxycarbonyl)-4-[N-methyl-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]piperidine (100 mg) in ethanol (2 mL) was added 4 M sodium hydroxide (8 mL). The mixture was refluxed overnight and extracted with chloroform. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and evaporated. The residue was subjected to a column of silica gel and liquid chromatography was performed using chloroform-methanol (20:1) to give the title compound as yellow syrup.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-aae653b7caa846f697d3b5cb12804893
Source dataset
uspto-grants-2002_12
Patent number
US06498169B1

Reaction notes

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