Formaldehyde → N-(4-Benzyloxy-benzyl)-6-(ethoxymethyl-amino)-nicotinamide

HRID 2079967Notes

Reaction equation

HRID 2079967 reaction equation
[NH2:1][C:2]1[CH:25]=[CH:24][C:5]([C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:12][CH:11]=2)=[O:7])=[CH:4][N:3]=1.C=O.O.[C:29]([O:32][CH2:33]C)(=O)[CH3:30]>C(O)C>[CH2:17]([O:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][NH:8][C:6](=[O:7])[C:5]2[CH:24]=[CH:25][C:2]([NH:1][CH2:33][O:32][CH2:29][CH3:30])=[N:3][CH:4]=2)=[CH:11][CH:12]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 8857Ethyl AcetateHCID 231305886-amino-N-(4-benzyloxy-benzyl)-nicotinamide

Product 1

HCID 23130644N-(4-Benzyloxy-benzyl)-6-(ethoxymethyl-amino)-nicotinamideYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the resulting 6-amino-N-(4-benzyloxy-benzyl)-nicotinamide (200 mg, 0.556 mmol) in ethanol (10 mL) were added 5,5-dimethylimidazophospho-2,4-dione (85 mg, 0.66 mmol) and 37% formaldehyde aqueous solution (1 mL), and the solution was stirred for 1 hour under reflux. Water and ethyl acetate were added to the reaction solution, which was then partitioned, and the organic layer was washed twice. NH silica gel was added to the organic layer, the solvent was evaporated in vacuo for adsorption, purification was carried out by NH silica gel column chromatography (ethyl acetate), and the title compound (95 mg, 0.243 mmol, 40%) was obtained as a white solid.

Workup

  1. temperatureunder reflux
  2. customwas then partitioned
  3. washthe organic layer was washed twice
  4. additionNH silica gel was added to the organic layer
  5. customthe solvent was evaporated in vacuo for adsorption, purification

Sources & evidence

ORD record
ord-4ec199a9154a49beb42858092c722d04
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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