Benzylamine → N-benzyl-2-(1,3-dioxolan-2-yl)ethanamine

HRID 874829Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 874829
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.Br[CH2:19][CH2:20][CH:21]1[O:25][CH2:24][CH2:23][O:22]1>C(#N)C.C(OCC)(=O)C>[CH2:1]([NH:8][CH2:19][CH2:20][CH:21]1[O:25][CH2:24][CH2:23][O:22]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 877762-(2-Bromoethyl)-1,3-dioxolane

Produkt 1

HCID 11769681N-benzyl-2-(1,3-dioxolan-2-yl)ethanamineAusbeute 40,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of benzylamine (2.18 mL, 20.0 mmol) and di-iso-propylethylamine (2.61 mL, 15.0 mmol) in acetonitrile (30 mL) was added 2-(2-bromoethyl)-1,3-dioxolane (1.17 mL, 10.0 mmol). The reaction mixture was stirred at room temperature for 72 hours. The reaction mixture was diluted with ethyl acetate and washed with water and brine. The organic phase was dried (magnesium sulfate), filtered and the solvent evaporated at reduced pressure. The residue was purified by flash column chromatography eluting with 0 to 4% methanol/dichloromethane to afford the title compound (0.836 g, 40%).

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialThe organic phase was dried (magnesium sulfate)
  3. filtrationfiltered
  4. customthe solvent evaporated at reduced pressure
  5. customThe residue was purified by flash column chromatography
  6. washeluting with 0 to 4% methanol/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-a0285b814ca049f996ac3f2e4bd4e2b1
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08980913B2

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