Morpholine → 6-Morpholino-1,4-heptadiene

HRID 46804

Reaktionsgleichung

Reaktionsgleichung von HRID 46804
[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

Komponenten

6

Edukt 3

HCID 8083MorpholineHCID 11641BromoetheneHCID 622041,3-Pentadiene

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 80271Tri-o-tolylphosphineKatalysatorHCID 167845palladium(II) acetateKatalysator

Versuchsvorschrift

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.

Quellen und Nachweise

ORD-Eintrag
ord-cd504876b1a94d00aab4292b727c1e02
Quelldatensatz
uspto-grants-1979_11
Patentnummer
US04175187

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