Aniline → N,N-Di(6-hydroxyhexyl)aniline

HRID 10911

Reaktionsgleichung

Reaktionsgleichung von HRID 10911
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15].[C:16](=[O:19])([O-])[O-].[K+].[K+]>C(O)CCC>[OH:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][N:1]([CH2:4][CH2:3][CH2:2][CH2:7][CH2:6][CH2:16][OH:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 6115AnilineHCID 11430Potassium CarbonateHCID 748286-Chloro-1-hexanol

Produkt 1

HCID 21982671N,N-Di(6-hydroxyhexyl)anilineAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

A mixture of 9.3 g (100 mmol) freshly distilled aniline, 30.0 g (220 mmol) 6-chloro-1-hexanol and 30.4 g (220 mmol) potassium carbonate were heated in 50 ml of n-butanol under reflux for 4 days. After cooling the solids were filtered of and the solvent is removed in vacuum. Purification by liquid chromatography (ethyl acetate/hexane 2:1) afforded 17.6 g (60%) of a colorless oil.1 H-NMR (400 MHz, CDCl3): δ=7.18 (m, 2H), 6.61 (m, 3H), 3.91 (t, J=6.4 Hz, 4H), 3.67 (t, J=6.4 Hz, 4H), 1.90–1.77 (m, 4H), 1.70–1.53 (m, 4H), 1.50–1.31 (m, 8H). 13C-NMR (100 MHz, CDCl3); 148.19, 129.31, 115.33, 111.86, 62.793, 51.06, 32.78, 27.30, 27.05, 25.76. EI-MS: 293 (M+), 206 (M+-C5H10OH), 120 (M+-2 C5H10OH). Calcd for C18H31NO2: C, 79.67; H, 10.65; N, 4.77; O, 10.90

Aufarbeitung

  1. temperatureunder reflux for 4 days
  2. temperatureAfter cooling the solids
  3. filtrationwere filtered of and the solvent
  4. customis removed in vacuum
  5. customPurification by liquid chromatography (ethyl acetate/hexane 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-8c173cccf2294dd195a5d48fb56cd6ad
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094929B2

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