4-Pyridinecarboxaldehyde → (2-Pyridin-3-ylethyl)pyridin-4-ylmethylamine

HRID 68994

Reaction equation

HRID 68994 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.[NH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1.[BH4-].[Na+]>CO.O>[N:14]1[CH:15]=[CH:16][CH:17]=[C:12]([CH2:11][CH2:10][NH:9][CH2:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[CH:13]=1

Participants

6

Reactant 3

HCID 133894-PyridinecarboxaldehydeHCID 8540512-(Pyridin-3-yl)ethan-1-amineHCID 4311764Sodium borohydride

Product 1

HCID 60761584(2-Pyridin-3-ylethyl)pyridin-4-ylmethylamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

4-Pyridine carbaldehyde (5.36 g) and 3-(2-aminoethyl)pyridine (6.5 ml) were added to 100 ml of methanol. The mixture was stirred at room temperature for 7 hours. The mixture was cooled to 0° C., and sodium borohydride (2.8 g) was added thereto. The mixture was further stirred at 0° C. for an hour. Water was added to the reaction mixture and methanol was distilled off under reduced pressure. The residue was subjected to extraction using dichloromethane. The organic layer was washed with saturated saline, dried with anhydrous sodium sulfate, and was condensed under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate:methanol=95:5→85:5). The purified product was condensed under reduced pressure to give the title compound (10.03 g) as a colorless oily matter.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. stirringThe mixture was further stirred at 0° C. for an hour
  3. distillationwas distilled off under reduced pressure
  4. extractionThe residue was subjected to extraction
  5. washThe organic layer was washed with saturated saline
  6. dry with materialdried with anhydrous sodium sulfate
  7. customcondensed under reduced pressure
  8. customThe residue was purified by basic silica gel column chromatography (ethyl acetate:methanol=95:5→85:5)
  9. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-d4f48387114947c59fea3f727a7bc9b3
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Linked notes

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