Toluene → Tert-butyl 4-(2-oxo-2-(piperidin-1-yl)ethoxy)piperidine-1-carboxylate

HRID 1091791Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1091791
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.Cl[CH2:16][C:17]([N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:18].C1(C)C=CC=CC=1.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[O:18]=[C:17]([N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)[CH2:16][O:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 2223122-Chloro-1-piperidine-1-yl-ethanoneHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Produkt 1

HCID 57791806Tert-butyl 4-(2-oxo-2-(piperidin-1-yl)ethoxy)piperidine-1-carboxylateAusbeute 96,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

Tert-butyl 4-hydroxypiperidine-1-carboxylate (10 g, 49.69 mmol), tetrabutylammonium hydrogensulfate (0.844 g, 2.48 mmol) and 2-chloro-1-(piperidin-1-yl)ethanone (8.08 g, 49.69 mmol) were added to toluene (75 mL) to this was added sodium hydroxide (49.7 g, 496.86 mmol) in water (20 ml) and the reaction was stirred at 25° C. overnight. The reaction mixture was quenched with water (100 mL), extracted with Et2O (3×75 mL), the organic layer was dried over MgSO4, filtered and evaporated to afford the crude product as an orange liquid (15.60 g, 96% yield); 1H NMR (400.132 MHz, CDCl3) δ 1.49 (9H, s), 1.51-1.60 (2H, m), 1.61-1.68 (2H, m), 1.81-1.90 (3H, m), 3.05-3.13 (2H, m), 3.35-3.47 (2H, m), 3.50-3.62 (4H, m), 3.71-3.79 (2H, m), 3.80-3.89 (2H, m), 4.13-4.19 (2H, m).

Aufarbeitung

  1. customThe reaction mixture was quenched with water (100 mL)
  2. extractionextracted with Et2O (3×75 mL)
  3. dry with materialthe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-4947c64ec8474161a75f37212a7a533f
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129380B2

Notizen zur Reaktion

Wird geladen…