Piperidine → 1-(4-Bromobenzyl)piperidine

HRID 1816359Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1816359
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl.C(O)(=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 8082PiperidineHCID 707414-BromobenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 164950451-(4-Bromobenzyl)piperidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of 4-bromobenzaldehyde (5 g), piperidine (2.9 mL), and acetic acid (1.5 mL) in DCE (65 mL) was treated with sodium triacetoxyborohydride (6.9 g). After 27 h, the resulting mixture was treated with saturated aqueous sodium bicarbonate (50 mL), and extracted with DCM (2×50 mL). The combined organic phases were dried (magnesium sulfate) and evaporated. Kugelrohr distillation of the residue (160° C., 5 mm Hg) gave the title compound as a pale yellow oil (5.9 g).

Aufarbeitung

  1. extractionextracted with DCM (2×50 mL)
  2. dry with materialThe combined organic phases were dried (magnesium sulfate)
  3. customevaporated
  4. distillationKugelrohr distillation of the residue (160° C., 5 mm Hg)

Quellen und Nachweise

ORD-Eintrag
ord-76f6794fd1874c53a2bc6884bb9ff8c0
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06884803B2

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