Piperidine → 3-Bromo-5-(piperidin-1-ylmethyl)pyridine

HRID 30470

Reaktionsgleichung

Reaktionsgleichung von HRID 30470
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=O)[CH:5]=[N:6][CH:7]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[NH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([CH2:8][N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH:3]=1

Komponenten

5

Edukt 3

HCID 8082PiperidineHCID 27847345-Bromo-3-pyridinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 671888053-Bromo-5-(piperidin-1-ylmethyl)pyridineAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

5-Bromo-pyridine-3-carbaldehyde (0.190g, 1 mmol), NaB(OAc)3H (0.320 g, 1.50 mmol) and piperidine (0.090 g, 1.05 mmol) were suspended in DCM (8 mL) and the reaction mixture was stirred overnight at rt. The reaction was quenched by the addition of 1 M NaOH solution (5 mL) and the mixture was stirred for 1 h. The reaction mixture was extracted with DCM (3×15 mL). The organic extracts were combined, dried over Na2SO4, filtered, and concentrated to yield a crude oily product (0.18 g, 71%). This crude product was carried to the next step.

Aufarbeitung

  1. customThe reaction was quenched by the addition of 1 M NaOH solution (5 mL)
  2. stirringthe mixture was stirred for 1 h
  3. extractionThe reaction mixture was extracted with DCM (3×15 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f27ee76980884117baec2023d5ba8948
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423147B2

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