Acetic Acid → 4-((Morpholin-4-yl)methyl)benzonitrile

HRID 1190999Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1190999
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1)#[N:2].[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C(O)(=O)C.C([BH3-])#N.[Na+]>ClCCCl>[N:11]1([CH2:7][C:6]2[CH:9]=[CH:10][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 660424-CyanobenzaldehydeHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 2168644-((Morpholin-4-yl)methyl)benzonitrileAusbeute 79,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

Dissolve 4-cyanobenzaldehyde (5 g, 38.1 mmol), morpholine (4.15 g, 47.7 mmol) and acetic acid (2.2 mL, 38.1 mmol) in DCE (100 mL). Add sodium cyanoborohydride (3.59 g, 57.2 mmol), and stir the mixture overnight. Add water (100 mL), separate the layers and extract the aqueous layer with DCM (3×50 mL). Wash the combined organic extracts with brine, dry over Na2SO4, filter and concentrate in vacuo. Purify by chromatography on silica gel (80 g, pre-packed cartridge) eluting with hexane/EtOAc (1:0 to 1:2 over 1.25 h, 80 mL/min) to obtain the desired intermediate as a colorless oil (6.1 g, 79%). MS (APCI+) m/z: 203 (M+H)+.

Aufarbeitung

  1. customAdd water (100 mL), separate the layers
  2. extractionextract the aqueous layer with DCM (3×50 mL)
  3. washWash the combined organic extracts with brine
  4. dry with materialdry over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurify by chromatography on silica gel (80 g, pre-packed cartridge)
  8. washeluting with hexane/EtOAc (1:0 to 1:2 over 1.25 h, 80 mL/min)

Quellen und Nachweise

ORD-Eintrag
ord-58e7650f2a8a4da5968718530d568faf
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680091B2

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