4-Hydroxybenzaldehyde → 4-Piperidin-1-ylmethyl-phenol

HRID 1790010

Reaktionsgleichung

Reaktionsgleichung von HRID 1790010
[OH: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>[N:10]1([CH2:6][C:5]2[CH:8]=[CH:9][C:2]([OH:1])=[CH:3][CH:4]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Komponenten

7

Edukt 4

HCID 1264-HydroxybenzaldehydeHCID 8082PiperidineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 116369724-Piperidin-1-ylmethyl-phenol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of 4-hydroxybenzaldehyde (10 g), piperidine (8.9 mL), and acetic acid (4.7 mL) in DCE (200 mL) was treated with sodium triacetoxyborohydride (24 g). After 16 h, the resulting mixture was treated with saturated aqueous sodium bicarbonate (100 mL) and extracted with DCM (5×100 mL). The combined organic phases were dried (magnesium sulfate) and evaporated. Trituration of the residue with ethyl acetate gave the title compound as a white crystalline solid (5.5 g).

Aufarbeitung

  1. extractionextracted with DCM (5×100 mL)
  2. dry with materialThe combined organic phases were dried (magnesium sulfate)
  3. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-bb490914043a4089a4b4985a7be43596
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07071191B2

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