3-Phenylprop-2-Enal → N,N'-Dicinnamylidene-1,6-hexanediamine

HRID 892696Notes

Reaction equation

HRID 892696 reaction equation
[CH:1](=O)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:11]([NH2:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH2:17].O>C1(C)C=CC=CC=1>[C:4]1([CH:3]=[CH:2][CH:1]=[N:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][N:18]=[CH:1][CH:2]=[CH:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 3073-Phenylprop-2-EnalHCID 962WaterHCID 16402Hexamethylenediamine

Product 1

HCID 67325N,N'-Dicinnamylidene-1,6-hexanediamineYield 97%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Cinnamaldehyde (198.2 g, 1.5 mole) is carefully added to a solution of 1,6-hexanediamine (87.2 g, 0.75 mole) in toluene (400 ml). Slight exotherm to 60° C. is observed. The resulting solution is heated at reflux until water (27 ml, 1.5 mole) is evolved. Evaporation of the solution gives 250.7 g of a brown viscous oil. 1H NMR: δ 1.0-2.85 (broad bands 8H); δ 3.6 (triplet 4 H); δ 6.82-8.22 (broad multiplete 16 H). Elemental analysis: Theory for C24H28N2 : C,83.72; H,8.14; N,8.14%. Found: C,83.61; H,8.35; N,8.05%.

Workup

  1. customto 60° C.
  2. temperatureThe resulting solution is heated
  3. customEvaporation of the solution

Sources & evidence

ORD record
ord-c93b0c5039a742e7a6ce114e1e81114a
Source dataset
uspto-grants-1992_06
Patent number
US05120356

Reaction notes

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