Benzaldehyde → Dibenzylamine

HRID 325758Notes

Reaction equation

HRID 325758 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.P(O)(O)O.C(N(CC)CC)C.[OH-].[Na+]>O>[CH2:1]([NH:16][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 240BenzaldehydeHCID 7504BenzylamineHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 107909Phosphorous acid

Product 1

HCID 7656DibenzylamineYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The imine from benzaldehyde and benzylamine (19.5 g; 0.1 mole) was heated with phosphorous acid (8.2 g; 0.1 mole) and triethylamine (10.1 g; 0.1 mole) for 2 hours at reflux (125°-130°). After cooling to 90° the reaction mixture was diluted with water (50 ml), basified (NaOH) and extracted with chloroform. The extract was concentrated by evaporation of the chloroform and triethylamine to yield dibenzylamine 19.3 g (98% yield).

Workup

  1. temperatureat reflux (125°-130°)
  2. temperatureAfter cooling to 90° the reaction mixture
  3. extractionextracted with chloroform
  4. concentrationThe extract was concentrated by evaporation of the chloroform and triethylamine

Sources & evidence

ORD record
ord-275c7b0824a14fd9a2f2fc6043d61885
Source dataset
uspto-grants-1984_04
Patent number
US04442286

Reaction notes

Loading…