Dimethylformamide → 3-Morpholin-4-ylmethyl-1H-pyrrole-2-carbaldehyde

HRID 241709

Reaktionsgleichung

Reaktionsgleichung von HRID 241709
CN([CH:4]=[O:5])C.O=P(Cl)(Cl)Cl.[NH:11]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[CH:12]1.C([O-])(=O)C.[Na+].[OH-].[Na+]>C(Cl)Cl>[N:17]1([CH2:16][C:13]2[CH:14]=[CH:15][NH:11][C:12]=2[CH:4]=[O:5])[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1

Komponenten

7

Edukt 5

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 575870184-(1H-Pyrrol-3-ylmethyl)-morpholine

Produkt 1

HCID 866508243-Morpholin-4-ylmethyl-1H-pyrrole-2-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

To a solution of DMF (66 mmoles) in DCM there is added, dropwise, at 0° C., POCl3. After stirring for 5 minutes, a solution of the compound obtained in Step B (33 mmoles) in DCM (60 ml) is added dropwise. After stiffing for 4 hours at 0° C. and for 30 minutes at reflux, an aqueous solution of sodium acetate (110 mmoles) is added. After a further 30 minutes at reflux, aqueous 2M sodium hydroxide solution is added at ambient temperature until the pH is alkaline (9-10). The solution is stirred for 2 hours at ambient temperature, and then 300 ml of DCM are added. After extracting with DCM, the organic phase is washed with water and with saturated aqueous NaCl solution, dried over sodium sulphate, filtered and evaporated to dryness. The residue obtained is purified by flash chromatography on silica gel (SiO2; gradient DCM/AcOEt) to yield the title product.

Aufarbeitung

  1. customat 0° C.
  2. waitAfter stiffing for 4 hours at 0° C. and for 30 minutes
  3. temperatureat reflux
  4. temperatureAfter a further 30 minutes at reflux
  5. stirringThe solution is stirred for 2 hours at ambient temperature
  6. extractionAfter extracting with DCM
  7. washthe organic phase is washed with water and with saturated aqueous NaCl solution
  8. dry with materialdried over sodium sulphate
  9. filtrationfiltered
  10. customevaporated to dryness
  11. customThe residue obtained
  12. customis purified by flash chromatography on silica gel (SiO2; gradient DCM/AcOEt)

Quellen und Nachweise

ORD-Eintrag
ord-0818ab0a767043628856676439b60624
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653073B2

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