Hydrochloric Acid → 1-Dimethylamino-4-[1-(1-ethoxy-ethoxy)-2-phenylethyl]cyclohexanecarbonitrile

HRID 2063719

Reaktionsgleichung

Reaktionsgleichung von HRID 2063719
[CH3:1][NH:2][CH3:3].Cl.[CH2:5]([O:7][CH:8]([O:10][CH:11]([CH:19]1[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]1)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:9])[CH3:6].[C-:26]#[N:27].[K+]>CO.O1CCCC1.O>[CH3:1][N:2]([CH3:3])[C:22]1([C:26]#[N:27])[CH2:23][CH2:24][CH:19]([CH:11]([O:10][CH:8]([O:7][CH2:5][CH3:6])[CH3:9])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:20][CH2:21]1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 9032Potassium CyanideHCID 668875294-[1-(1-Ethoxy-ethoxy)-2-phenylethyl]cyclohexanone

Produkt 1

HCID 698102431-Dimethylamino-4-[1-(1-ethoxy-ethoxy)-2-phenylethyl]cyclohexanecarbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittel2×HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

40% aqueous dimethylamine solution (6.05 ml, 47.9 mmol) was added to a mixture of 4 M hydrochloric acid (2.61 ml) and methanol (1.56 ml), while cooling with ice. A solution of 4-[1-(1-ethoxy-ethoxy)-2-phenylethyl]cyclohexanone (2.91 g, 10.0 mmol) in methanol (6 ml) and tetrahydrofuran (3 ml) was added to this mixture. Thereafter, potassium cyanide (1.56 g, 24.1 mmol) was added to the mixture, the mixture was stirred at room temperature overnight, water (150 ml) was then added and the mixture was extracted with diethyl ether (4×50 ml). The combined organic phases were dried with sodium sulfate and concentrated i. vac. The residue was taken up in methylene chloride (50 ml) and the mixture was washed with water (30 ml). The organic phase was dried again with sodium sulfate and concentrated i. vac.

Aufarbeitung

  1. temperaturewhile cooling with ice
  2. extractionthe mixture was extracted with diethyl ether (4×50 ml)
  3. dry with materialThe combined organic phases were dried with sodium sulfate
  4. concentrationconcentrated i
  5. washthe mixture was washed with water (30 ml)
  6. dry with materialThe organic phase was dried again with sodium sulfate
  7. concentrationconcentrated i

Quellen und Nachweise

ORD-Eintrag
ord-21c484039fc04503b1778d68549300f2
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288406B2

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