Benzaldehyde → N-benzylpiperidine-4-carboxamide

HRID 1821742

Reaktionsgleichung

Reaktionsgleichung von HRID 1821742
[NH:1]1[CH2:9][CH2:8][CH:4]([C:5]([NH2:7])=[O:6])[CH2:3][CH2:2]1.[CH:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.O>[CH2:10]([NH:7][C:5](=[O:6])[CH:4]1[CH2:8][CH2:9][NH:1][CH2:2][CH2:3]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

6

Edukt 3

HCID 240BenzaldehydeHCID 37724-PiperidinecarboxamideHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 3868064N-benzylpiperidine-4-carboxamideAusbeute 51,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of isonipecotamide (12.3 g, 96 mmol) in 200 mL of dichloromethane, was added, benzaldehyde (10.6 g, 100 mmol) and sodium triacetoxyborohydride (29.7 gm, 140 mmol) and the mixture was stirred at room temperature for 5 days. The thick white mixture was diluted with 100 mL water and extracted with EtOAc (2×20 mL) The aqueous phase was basified with 1N NaOH to pH 22 12. The resulting white precipitate was collected by suction filtration. The white solid was subsequently taken up in 50 mL of EtOAc, and was washed with 20 mL of brine, then dried (MgSO4), filtered and concentrated to give 10.84 g (50%) of the desired product.

Aufarbeitung

  1. additionwas added
  2. extractionextracted with EtOAc (2×20 mL) The aqueous phase
  3. filtrationThe resulting white precipitate was collected by suction filtration
  4. washwas washed with 20 mL of brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9f6ced7b52864182937ca60b840dfc01
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07608618B2

Verknüpfte Notizen

Wird geladen…