1H-Benzimidazole-2-carboxaldehyde → (1H-benzimidazol-2-ylmethylene)(1-methylpiperidin-4-yl)amine

HRID 572829

Reaction equation

HRID 572829 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]=O.[NH2:12][CH:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1>C(O)C>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]=[N:12][CH:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 768261H-Benzimidazole-2-carboxaldehydeHCID 27375314-Amino-1-methylpiperidine

Product 1

HCID 136335844(1H-benzimidazol-2-ylmethylene)(1-methylpiperidin-4-yl)amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1H-Benzimidazole-2-carboxaldehyde (781 mg, can be prepared according to Fegy, K. Angewandte Chemie Int Ed, 1998, vol. 37, 1270-1273), 4-amino-1-methylpiperidine (781 mg) and 4 Å molecular sieves (15 g) in ethanol (100 mL) are heated under reflux for 4 h. The mixture is then filtered and the filtrate concentrated under reduced pressure to yield (1H-benzimidazol-2-ylmethylene)(1-methylpiperidin-4-yl)amine as a beige solid.

Workup

  1. temperatureunder reflux for 4 h
  2. filtrationThe mixture is then filtered
  3. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-09ad8afe261641bbbf1993569c1c8080
Source dataset
uspto-grants-2015_05
Patent number
US09029357B2

Linked notes

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