4-(Aminomethyl)piperidine → Methyl 3-(3-cyanophenyl)-5-[(piperidin-4-ylmethyl)aminomethyl]benzoate

HRID 1862574Notes

Reaction equation

HRID 1862574 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]([CH:16]=[C:17]([CH:19]=O)[CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:7][CH:8]=1)#[N:2].[NH2:21][CH2:22][CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>C1(C)C=CC=CC=1>[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]([CH:16]=[C:17]([CH2:19][NH:21][CH2:22][CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 235274-(Aminomethyl)piperidineHCID 9795280Methyl 3-(3-cyanophenyl)-5-(formyl)benzoate

Product 1

HCID 18620001Methyl 3-(3-cyanophenyl)-5-[(piperidin-4-ylmethyl)aminomethyl]benzoateYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 20 ml of toluene, were added 1.0 g of the compound obtained in Example 11 and 500 mg of 4-aminomethylpiperidine. The resulting mixture was refluxed using a Dean-Stark device under heating for 2 hours to remove the produced water. The solvent was then evaporated, and 20 ml of anhydrous methanol was added to dissolve the residue. To the obtained solution, was added 100 mg of 5% palladium-carbon. The mixture was stirred at room temperature under hydrogen atmosphere. After 4 hours, 200 mg of the 5% palladium-carbon was further added, and the reaction mixture was stirred for another 65 hours. The catalyst was separated by filtration, and the reaction mixture was concentrated. The resulting concentrate was then dissolved in a mixed solvent of water-dichloromethane, and the aqueous layer was separated and concentrated to afford 0.82 g (60%) of the title compound as a light-yellow oily substance.

Workup

  1. temperatureThe resulting mixture was refluxed
  2. temperatureunder heating for 2 hours
  3. customto remove the produced water
  4. customThe solvent was then evaporated
  5. addition20 ml of anhydrous methanol was added
  6. dissolutionto dissolve the residue
  7. additionTo the obtained solution, was added 100 mg of 5% palladium-carbon
  8. addition200 mg of the 5% palladium-carbon was further added
  9. stirringthe reaction mixture was stirred for another 65 hours
  10. customThe catalyst was separated by filtration
  11. concentrationthe reaction mixture was concentrated
  12. concentrationThe resulting concentrate
  13. dissolutionwas then dissolved in a mixed solvent of water-dichloromethane
  14. customthe aqueous layer was separated
  15. concentrationconcentrated

Sources & evidence

ORD record
ord-f432bc91727e43e0aad9be67a5b4ebd0
Source dataset
uspto-grants-2003_03
Patent number
US06538137B1

Reaction notes

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