Benzylamine → 73325-67-4

HRID 325755Notes

Reaction equation

HRID 325755 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.[CH2:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.P(O)(O)O.[OH-].[Na+]>O>[CH2:9]([NH:16][CH2:7][C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 133894-PyridinecarboxaldehydeHCID 14798Sodium HydroxideHCID 107909Phosphorous acid

Product 1

HCID 96434573325-67-4Yield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the imine from pyridine-4-carboxaldehyde and benzylamine (20 g; 0.1 mole) was added phosphorous acid (8.4 g; 0.1 mole) and the mixture heated at 110°-130° for 11/2 hours. After cooling to 90° water (150 ml) was added. The aqueous solution was basified with NaOH and extracted with benzene (3×100 ml). Evaporation of the solvent gave the N-benzyl(4-pyridyl) methylamine 14.9 g (74%). Nmr measurements, 1H and 13C, confirmed the structural assignment.

Workup

  1. temperaturethe mixture heated at 110°-130° for 11/2 hours
  2. additionwas added
  3. extractionextracted with benzene (3×100 ml)
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-dfb8cb7fef5949118eb1c1bf1fe1b5bc
Source dataset
uspto-grants-1984_04
Patent number
US04442286

Reaction notes

Loading…