Morpholine → 6-Morpholino-1,4-heptadiene

HRID 46804

Reaction equation

HRID 46804 reaction equation
[CH:1](Br)=[CH2:2].[CH2:4]=[CH:5]/[CH:6]=[CH:7]/[CH3:8].[NH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[O:12]1[CH2:13][CH2:14][N:9]([CH:1]([CH3:2])[CH:4]=[CH:5][CH2:6][CH:7]=[CH2:8])[CH2:10][CH2:11]1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 11641BromoetheneHCID 622041,3-Pentadiene

Product 1

HCID 537288196-Morpholino-1,4-heptadieneYield 52%

Reagents, catalysts & solvents 2

HCID 80271Tri-o-tolylphosphineCatalystHCID 167845palladium(II) acetateCatalyst

Procedure

Vinyl bromide, E-1,3-pentadiene, and morpholine reacted with one mole percent palladium acetate - two mole percent tri-o-tolylphosphine as catalyst in 17 hrs. at 100° C. to form 6-morpholino-1,4-heptadiene in 52% yield. (All yields hereinafter reported, except where otherwise noted, are of purified, isolated products.) In this instance a 3:1 ratio of diene to vinylic halide was used, it being found that better yields were obtained thereby than with the lower 1.25:1 ratio. The remainder of the product was polymer and higher boiling materials which were not identified.

Sources & evidence

ORD record
ord-cd504876b1a94d00aab4292b727c1e02
Source dataset
uspto-grants-1979_11
Patent number
US04175187

Linked notes

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