Isobutyraldehyde → n-benzyl-2-methylpropan-1-amine

HRID 225042Notes

Reaction equation

HRID 225042 reaction equation
[CH:1](=O)[CH:2]([CH3:4])[CH3:3].[CH2:6]([NH2:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.P(O)(O)O>O>[CH2:6]([NH:13][CH2:1][CH:2]([CH3:4])[CH3:3])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 6561IsobutyraldehydeHCID 7504BenzylamineHCID 107909Phosphorous acid

Product 1

HCID 211729n-benzyl-2-methylpropan-1-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the imine from isobutyraldehyde and benzylamine (51.4 g; 0.3 mole) was added phosphorous acid (24.6 g; 0.3 mole). While stirring the mixture was slowly warmed to 65°-70° when a vigorous exothermic reaction was initiated. The reaction temperature reached 130°-145°. Upon cooling the reaction mixture became a glass. This glass was dissolved in water and basified. Extraction with benzene yielded benzylisobutylamine. The aqueous portion was acidified and after removal of sodium chloride yielded a phosphonic acid (20 g). Recrystallization gave a white solid (12 g) mp 186°-190° the N-benzyl α-aminophosphonic acid. ##STR35##

Workup

  1. temperaturewas slowly warmed to 65°-70° when
  2. customa vigorous exothermic reaction
  3. customreached 130°-145°
  4. temperatureUpon cooling the reaction mixture
  5. extractionExtraction with benzene

Sources & evidence

ORD record
ord-c4b49112a199428c8473cdf55ff1b8ff
Source dataset
uspto-grants-1980_11
Patent number
US04235809

Reaction notes

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