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4,4'-Bipiperidine dihydrochloride → 4,4'-Bipiperidine, 1-boc protected

HRID 494014
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 494014
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH2:5][CH2:4]1.[C:15](OC([O-])=O)([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]>C(O)C.[OH-].[Na+]>[NH:3]1[CH2:8][CH2:7][CH:6]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH2:5][CH2:4]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 122706374,4'-Bipiperidine dihydrochlorideHCID 22064466Tert-butyldicarbonate

Produkt 1

HCID 117475994,4'-Bipiperidine, 1-boc protectedAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

A solution is prepared of 41 g (0.17 M) of 4,4′-bipiperidine dihydrochloride in 250 ml of ethanol and 250 ml of 2N sodium hydroxide. A solution of 18.5 g (0.085 M) of t-butyl dicarbonate in 100 ml of ethanol are added slowly, at 0° C. The reaction mixture is agitated for 1 hour at 10° C. and the ethanol is then removed by an evaporator, under reduced pressure. The residual aqueous phase is saturated with sodium chloride and extracted with ethyl acetate. The organic phase obtained is dried over magnesium sulphate and concentrated under reduced pressure. The crude product is purified by silica gel chromatography in eluting with the aid of a dichloromehane/methanol/aqueous ammonia mixture (8/2/0.4; v/v/v). 16.5 g of the compound sought after are thus obtained as a white solid (yield=72%).

Aufarbeitung

  1. customthe ethanol is then removed by an evaporator, under reduced pressure
  2. extractionextracted with ethyl acetate
  3. customThe organic phase obtained
  4. dry with materialis dried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product is purified by silica gel chromatography
  7. washin eluting with the aid of a dichloromehane/methanol/aqueous ammonia mixture (8/2/0.4; v/v/v)

Quellen und Nachweise

ORD-Eintrag
ord-c75086f5b7984dd5a4371536ebd168c0
Quelldatensatz
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07538111B2

Notizen zur Reaktion

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