2-Chloro-N,N-dimethylethylamine → Dimethyl[2-(2-phenylchroman-6-yloxy)ethyl]amine

HRID 31167

Reaktionsgleichung

Reaktionsgleichung von HRID 31167
C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][N:8]([CH3:12])[CH2:9][CH2:10]Cl.[C:13]1([CH:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24]([OH:29])[CH:25]=3)[O:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(OCC)(=O)C.C(#N)C>[CH3:7][N:8]([CH3:12])[CH2:9][CH2:10][O:29][C:24]1[CH:25]=[C:26]2[C:21](=[CH:22][CH:23]=1)[O:20][CH:19]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:28][CH2:27]2

Komponenten

6

Edukt 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 10796Cesium carbonateHCID 212875382-Phenylchroman-6-ol

Produkt 1

HCID 17978584Dimethyl[2-(2-phenylchroman-6-yloxy)ethyl]amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Cesium carbonate (230 mg) and an excess of 2-(dimethylamino)ethyl chloride in ethyl acetate were added into a solution of 2-phenylchroman-6-ol (150 mg) in acetonitrile (5 ml). The reaction mixture was refluxed for 30 minutes. After removing the solvents, the residue was taken up in water and extracted with ethyl acetate. The combined organic layers were washed with water and then with saturated NaCl-solution and dried with Na2SO4. The dimethyl[2-(2-phenylchroman-6-yloxy)-ethyl]amine was crystallised from heptane. 1H NMR (400 MHz, d6-DMSO) δ: 7.43-7.30 (m, 5H), 6.75-6.67 (m, 3H), 5.03 (dd, 1H, J 10.0, 2.2 Hz), 3.95 (t, 2H, J 5.9 Hz), 2.94 (ddd, 1H, J −16.7, 10.9, 5.8 Hz), 2.69 (ddd, 1H, J −16.7, 5.2, 3.3 Hz), 2.58 (t, 2H, J 5.9 Hz), 2.13 (m, 1H), 1.96 (m, 1H).

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 30 minutes
  2. customAfter removing the solvents
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with water
  5. dry with materialwith saturated NaCl-solution and dried with Na2SO4
  6. customThe dimethyl[2-(2-phenylchroman-6-yloxy)-ethyl]amine was crystallised from heptane

Quellen und Nachweise

ORD-Eintrag
ord-114c319582744b84bd6f0d497c324daf
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425568B2

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