Dibenzylamine → Ethyl 2-(dibenzylamino)acetate

HRID 530543

Reaktionsgleichung

Reaktionsgleichung von HRID 530543
Cl[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH2:8]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CCO>[CH2:16]([N:15]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

4

Edukt 2

HCID 7656DibenzylamineHCID 7751Ethyl chloroacetate

Produkt 1

HCID 3553452Ethyl 2-(dibenzylamino)acetateAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a stirred solution of ethyl chloroacetate (1.0 g, 8.16 mmol) in EtOH (5.0 mL), dibenzylamine (2.09 g, 10.6 mmol) was added and the mixture heated at 140° C. in a microwave reactor for 20 min. After evaporation of the solvent, the crude was dissolved in CH2Cl2 and washed with a 1.0 M KOH solution and brine, then dried over Na2SO4, filtered, and concentrated in vacuo to give a crude product, as an oil. Purification by column chromatography using a Teledyne ISCO apparatus, eluting with Cy:EtOAc (98:2), gave the title compound (1.85 g, 80%), as a white solid. MS (ESI) m/z: 284 [M−H]+[1H NMR as previously reported in literature: Synthesis, 1985, 9, 850-855].

Aufarbeitung

  1. customAfter evaporation of the solvent
  2. dissolutionthe crude was dissolved in CH2Cl2
  3. washwashed with a 1.0 M KOH solution and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a crude product
  8. customPurification by column chromatography
  9. washeluting with Cy

Quellen und Nachweise

ORD-Eintrag
ord-86bb5952c5f04e7f9726edcf2814dd69
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353075B2

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