Methanol → 2-(4-Methoxyphenethylamino)cyclohexanol

HRID 130882

Reaktionsgleichung

Reaktionsgleichung von HRID 130882
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[OH:8].C([O-])([O-])=O.[K+].[K+].Cl[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1.CO>CN(C=O)C>[CH3:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][CH2:16][NH:1][CH:2]2[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]2[OH:8])=[CH:19][CH:20]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 232862-AminocyclohexanolHCID 875134-(2-Chloroethyl)phenyl methyl ether

Produkt 1

HCID 607146502-(4-Methoxyphenethylamino)cyclohexanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Mix (±)-2-aminocyclohexanol (1.5227 g, 13.2 mmol), K2CO3 (4.56 g, 33.0 mmol), and 1-(2-chloroethyl)-4-methoxybenzene (2.0 mL, 13.2 mmol) in DMF (30 mL). Heat at 100° C. for 24 hours. Cool down to room temperature and filtrate with MeOH wash. Concentrate and remove DMF azeotropically with xylenes. Take up the residue in CH2Cl2 and H2O (100 mL each). Separate the layers and extract the aqueous layer with CH2Cl2 (2×100 mL). Wash the organic layers with H2O and brine (100 mL each). Dry the combined organic layers over MgSO4, concentrate and purify by flash chromatography, eluting with 50:45:5 EtOAc/CH2Cl2/2.0 M NH3 in MeOH to afford 2-(4-methoxyphenethylamino)cyclohexanol. (1.38 g, 42%).

Aufarbeitung

  1. washwash
  2. concentrationConcentrate
  3. customremove DMF azeotropically with xylenes
  4. customSeparate the layers
  5. extractionextract the aqueous layer with CH2Cl2 (2×100 mL)
  6. washWash the organic layers with H2O and brine (100 mL each)
  7. dry with materialDry the combined organic layers over MgSO4
  8. concentrationconcentrate
  9. custompurify by flash chromatography
  10. washeluting with 50:45:5 EtOAc/CH2Cl2/2.0 M NH3 in MeOH

Quellen und Nachweise

ORD-Eintrag
ord-02ecfa8e9a624065a593c932350603ad
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07381719B2

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