1,3-Butadiene → 3-Methyl-12-phenyl-1-aza-1,5,9-cyclododecatriene

HRID 1154073Notes

Reaction equation

HRID 1154073 reaction equation
[CH:1](=[N:8][CH:9]=[CH:10][CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:12]=[CH:13][CH:14]=[CH2:15]>>[CH3:11][CH:10]1[CH2:4][CH:3]=[CH:2][CH2:1][CH2:15][CH:14]=[CH:13][CH2:12][CH:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:8]=[CH:9]1

Participants

3

Reactant 2

HCID 78451,3-ButadieneHCID 143013N-benzylidene-propenylamine

Product 1

HCID 537330893-Methyl-12-phenyl-1-aza-1,5,9-cyclododecatriene

Procedure

In a manner analogous to that described in Example 1(a), 495 g (3.41 mols) of N-benzylidene-propenylamine is reacted with 1,3-butadiene. The reaction mixture is distilled to yield 750 g (2.97 mols) of 3-methyl-12-phenyl-1-aza-1,5,9-cyclododecatriene as a cis-trans isomeric mixture (cis:trans=65:35); b.p. 112°-113° C./1 Pa; nD20 =1.5505; m.p. (cis isomer)=57°-58° C.

Workup

  1. distillationThe reaction mixture is distilled

Sources & evidence

ORD record
ord-eb44a47316d54b6aaec0a0462e8bc5d7
Source dataset
uspto-grants-1984_12
Patent number
US04487947

Reaction notes

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