Didecylamine → N,N,N',N'-Tetradecyl-2-butene-1,4-diamine

HRID 275211

Reaktionsgleichung

Reaktionsgleichung von HRID 275211
[CH2:1]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C(O[CH2:26][CH:27]=[CH:28][CH2:29]OC(=O)C)(=O)C>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:12]([N:11]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:26][CH:27]=[CH:28][CH2:29][N:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:29][CH2:28][CH2:27][CH3:26])[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Komponenten

5

Edukt 2

HCID 14261DidecylamineHCID 1404022-Butene-1,4-diol diacetate

Produkt 1

HCID 54366770N,N,N',N'-Tetradecyl-2-butene-1,4-diamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of di-n-decylamine (10.9 g, 36.6 mmol) and 2-butene-1,4-diol diacetate (3.15 g, 18.3 mmol) in tetrahydrofuran (THF) (150 ml) is treated with tetrakis(triphenylphosphine)palladium(0) (1.0 g, 0.9 mmol) and stirred at room temperature overnight. The reaction mixture is concentrated in vacuo to a oil that is redissolved in THF (500 ml) and treated with 20% aqueous sodium hydroxide (250 ml). The mixture is stirred for one hour, concentrated, and extracted with ether. The ether extracts are dried and concentrated giving an orange oil which is purified by medium pressure chromatography (silica gel; 25% ethyl acetate in hexanes). The title compound is isolated as 5.8 g (49% yield) of a clear oil.

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated in vacuo to a oil that
  2. dissolutionis redissolved in THF (500 ml)
  3. additiontreated with 20% aqueous sodium hydroxide (250 ml)
  4. stirringThe mixture is stirred for one hour
  5. concentrationconcentrated
  6. extractionextracted with ether
  7. dry with materialThe ether extracts are dried
  8. concentrationconcentrated
  9. customgiving an orange oil which
  10. customis purified by medium pressure chromatography (silica gel; 25% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-094180197c384a0788740ca7dd012497
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05391808

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