4-Pyridinecarboxaldehyde → HCID 10343318, compound

HRID 969664Notes

Reaction equation

HRID 969664 reaction equation
[NH2:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:22])([CH:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)[CH3:14])=[CH:9][CH:8]=1)=[O:5].[N:27]1[CH:32]=[CH:31][C:30]([CH:33]=O)=[CH:29][CH:28]=1.[BH4-].[Na+]>CCO>[CH3:14][C:13]([C:10]1[CH:9]=[CH:8][C:7]([NH:6][C:4](=[O:5])[C:3]2[CH:23]=[CH:24][CH:25]=[CH:26][C:2]=2[NH:1][CH2:33][C:30]2[CH:31]=[CH:32][N:27]=[CH:28][CH:29]=2)=[CH:12][CH:11]=1)([CH:15]1[CH2:16][CH2:17][N:18]([CH3:21])[CH2:19][CH2:20]1)[CH3:22]

Participants

5

Reactant 3

HCID 133894-PyridinecarboxaldehydeHCID 4311764Sodium borohydrideHCID 69510665HCID 69510665, compound

Product 1

HCID 10343318HCID 10343318, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-N-{4-[1-methyl-1-(1-methyl-piperidin-4-yl)ethyl]phenyl}benzamide (600 mg, Step B) and 4-pyridinecarboxaldehyde (0.22 mL) was heated at reflux in EtOH (50 mL) overnight. NaBH4 (250 mg) was added and the mixture was heated at reflux for 10 min and evaporated. The residue was mixed with CH2Cl2 and washed with H2O twice, followed by brine. The organic layer was dried over Na2SO4 and evaporated under reduced pressure. The residue was purified by column chromatography using 10% MeOH/CH2Cl2 to provide the title compound. MS (ES+): 443 (M+H)+. Calc'd. for C28H34N4O-442.27.

Workup

  1. temperaturewas heated
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 10 min
  4. customevaporated
  5. additionThe residue was mixed with CH2Cl2
  6. washwashed with H2O twice
  7. dry with materialThe organic layer was dried over Na2SO4
  8. customevaporated under reduced pressure
  9. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-1c1a2b8012e747229cfa1d19629dbef4
Source dataset
uspto-grants-2007_12
Patent number
US07307088B2

Reaction notes

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