Benzaldehyde → [(benzylamino)-phenylmethyl]phosphonic acid

HRID 225043Notes

Reaction equation

HRID 225043 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:17]([OH:20])([OH:19])[OH:18]>N1C=CC=CC=1>[CH2:1]([NH:16][CH:9]([P:17](=[O:18])([OH:20])[OH:19])[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

5

Reactant 3

HCID 240BenzaldehydeHCID 7504BenzylamineHCID 107909Phosphorous acid

Product 1

HCID 4469578[(benzylamino)-phenylmethyl]phosphonic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The imine from benzaldehyde and benzylamine (19.5 g; 0.1 mole) was dissolved in pyridine (9 g) and phosphorous acid (8.2 g; 0.1 mole) was added. The mixture was heated at reflux for 3 hours, cooled, basified and extracted with benzene. The residue was acidified to yield a white solid. Crystallization gave N-benzyl α-amino benzylphosphonic acid mp 233°-4°. Phosphorus nmr of a basified aqueous solution gave a peak at -15.9 ppm (relative to 85% H3PO4) consistent with the assigned structure given in Example 1.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 hours
  3. temperaturecooled
  4. extractionextracted with benzene
  5. customto yield a white solid
  6. customCrystallization

Sources & evidence

ORD record
ord-c0142dff446548bdba71fb1ecaca463b
Source dataset
uspto-grants-1980_11
Patent number
US04235809

Reaction notes

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