Benzaldehyde → N-benzylpiperidine-4-carboxamide

HRID 1830724

Reaktionsgleichung

Reaktionsgleichung von HRID 1830724
[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>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. 1H-NMR (400 MHz, CDCl3) δ7.85 (m, 5H), 5.45 (s, 1H), 5.34 (s, 1H), 3.5 (s, 2H), 2.93 (d, J=10.96 Hz, 2H), 2.16 (t, J=12.13 Hz, 1H), 2.01 (t, J=11.74 Hz, 2H), 1.87 (d, J=12.52 Hz, 2H), 1.76 (q, J=12.52 Hz, 2H).

Aufarbeitung

  1. additionwas added
  2. extractionextracted with EtOAc (2×20 mL)
  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-b6e5831158794da89645e89ab4cd8afb
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07067506B2

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