Bromocyclopentane → 1-Cyclopentylpiperidin-4-ol

HRID 272845Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 272845
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+].[CH:14]1(Br)[CH2:18][CH2:17][CH2:16][CH2:15]1>CO>[CH:14]1([N:5]2[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]2)[CH2:18][CH2:17][CH2:16][CH2:15]1

Komponenten

5

Edukt 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 79341Piperidin-4-ol

Produkt 1

HCID 217027851-Cyclopentylpiperidin-4-olAusbeute 71,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

4-Hydroxypiperidine (2.08 g, 21.2 mmol), K2CO3 (5.86 g, 2 eq.), cylopentylbromide (11.51 g, 77.6 mmol, 3.7 eq.) and MeOH (20.8 ml) were refluxed together overnight. The reaction was allowed to cool to room temperature and quenched with 2M HCl solution (40 ml) and extracted with TBME (40 ml). The aqueous phase was basified to pH 14 with a 2M NaOH solution and extracted with DCM (4×50 ml). The combined organic extracts were dried over MgSO4, filtered, washed with DCM and concentrated in vacuo to give 1-cyclopentyl-4-hydroxypiperidine (2.55 g, 71%) as a pale yellow oil.

Aufarbeitung

  1. customquenched with 2M HCl solution (40 ml)
  2. extractionextracted with TBME (40 ml)
  3. extractionextracted with DCM (4×50 ml)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. washwashed with DCM
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fc9458b8f94b44a59a393f9bdb1cd505
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456164B2

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