P-Anisidine → 4-(p-Anisidino)-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine

HRID 395438Notes

Reaction equation

HRID 395438 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:18]=[C:17]([CH2:19][N:20]3[CH2:25][CH2:24][C:23](=O)[CH2:22][CH2:21]3)[CH:16]=[CH:15][N:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[CH3:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][CH:30]=1>C1(C)C=CC=CC=1>[CH3:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([NH:35][CH:23]2[CH2:24][CH2:25][N:20]([CH2:19][C:17]3[CH:16]=[CH:15][N:14]=[C:13]([C:5]4[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=4)[CH:18]=3)[CH2:21][CH2:22]2)=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 22557811[2-(3,4,5-Trimethoxyphenyl)pyridin-4-yl]methyl-4-piperidone

Product 1

HCID 120431454-(p-Anisidino)-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]-4-piperidone (2.17 g) in toluene (40 mL) was added p-anisidine (900 mg) and molecular sieves 4A (6.0 g). The mixture was refluxed overnight, then filtered and the filtrate was evaporated. The residual oil was dissolved in ethanol (40 mL) and sodium borohydride (276 mg) was added. The mixture was stirred at room temperature for 2 hours before concentration in vacuo. The residue was dissolved in ethyl acetate, washed with brine, dried over anhydrous sodium sulfate and evaporated. The residual oil was subjected to silica gel column chromatography using chloroform-methanol (50:1) to give the title compound as yellow amorphous.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. filtrationfiltered
  3. customthe filtrate was evaporated
  4. dissolutionThe residual oil was dissolved in ethanol (40 mL)
  5. additionsodium borohydride (276 mg) was added
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. washwashed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-5c7a64c3fb98414899a29c9a79899491
Source dataset
uspto-grants-2003_08
Patent number
US06605620B1

Reaction notes

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