Formaldehyde → N-[(Piperidin-1-yl)methyl]benzenecarboximidic acid

HRID 1957922Notes

Reaction equation

HRID 1957922 reaction equation
[C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.[CH2:16]=O>CO>[N:10]1([CH2:16][NH:9][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 2331BenzamideHCID 8082Piperidine

Product 1

HCID 100673N-[(Piperidin-1-yl)methyl]benzenecarboximidic acidYield 893.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Benzamide (0.5 g, 0.4 mmol) was dissolved in 5 mL of methanol. To this stirred solution piperidine (0.35 mL, 0.4 mol) was added and the resulting solution was cooled in an ice bath. Formaldehyde (0.31 mL, 0.4 mol, 37% in water) was added dropwise. The solution was stirred for 10 min and then it was refluxed for 4 h. After cooling, the solvents were evaporated to give Mannich base 15 as a white solid 0.78 g (87% yield).

Workup

  1. temperaturethe resulting solution was cooled in an ice bath
  2. temperatureit was refluxed for 4 h
  3. temperatureAfter cooling
  4. customthe solvents were evaporated

Sources & evidence

ORD record
ord-3660bc308f124ea9a926c90fd16e0588
Source dataset
uspto-grants-2013_04
Patent number
US08410075B2

Reaction notes

Loading…