Aniline → 1,2-Ethanediamine, N1,N1-diethyl-N2-phenyl-

HRID 1833982Notes

Reaction equation

HRID 1833982 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]([N:10]([CH2:14][CH3:15])[CH2:11][CH2:12]O)[CH3:9].P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1>O>[CH2:8]([N:10]([CH2:14][CH3:15])[CH2:11][CH2:12][NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:9]

Participants

5

Reactant 3

HCID 6115AnilineHCID 7497DiethylethanolamineHCID 7540Triphenyl phosphite

Product 1

HCID 742711,2-Ethanediamine, N1,N1-diethyl-N2-phenyl-Yield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

93 parts of aniline, 180 parts of 2-diethylaminoethanol and 10 parts of triphenyl phosphite are heated for 20 hours at 210° C in a stirred autoclave. The autoclave is then let down and the water of reaction formed, the excess aniline and the unconverted aminoalcohol are distilled under reduced pressure. 144 parts of N-(β-diethylaminoethyl)-aniline, corresponding to a yield of 75% of theory, distil at a boiling point of 185° - 187° C/15 mm Hg.

Workup

  1. customformed
  2. distillationthe excess aniline and the unconverted aminoalcohol are distilled under reduced pressure
  3. custom144 parts of N-(β-diethylaminoethyl)-aniline, corresponding to a yield of 75% of theory, distil at a boiling point of 185° - 187° C/15 mm Hg

Sources & evidence

ORD record
ord-39ae96c447434b8286ff1d0132d5d3b3
Source dataset
uspto-grants-1978_01
Patent number
US04067903

Reaction notes

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