Carbamic acid, ethyl-, ethyl ester → 1-(4-Bromo-2-ethoxybenzyl)-piperidine

HRID 1505896Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1505896
[H-].[Na+].[Br:3][C:4]1[CH:16]=[CH:15][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[C:6](F)[CH:5]=1.C(NC([O:23][CH2:24][CH3:25])=O)C>O1CCOCC1.O>[Br:3][C:4]1[CH:16]=[CH:15][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[C:6]([O:23][CH2:24][CH3:25])[CH:5]=1

Komponenten

6

Edukt 3

HCID 12195Carbamic acid, ethyl-, ethyl esterHCID 24758Sodium hydrideHCID 534861121-(4-Bromo-2-fluorobenzyl)piperidine

Produkt 1

HCID 582664591-(4-Bromo-2-ethoxybenzyl)-piperidineAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

Sodium hydride (306 mg, 60%, 7.6 mmol) was added in portions to a solution of 1-(4-bromo-2-fluorobenzyl)-piperidine (520 mg, 1.9 mmol) and ethyl urethane (0.91 mL, 7.6 mmol) in dioxane (10 mL) under an atmosphere of nitrogen. The reaction mixture was then sonicated for 30 minutes until gas evolution ceased then heated at 140° C. overnight in a sealed tube. The reaction mixture was diluted with water and extracted with DCM (3×30 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford a colourless oil that was then purified by flash chromatography (silica, 12 g column, ISCO, 0-10% methanol in DCM) to afford the title compound as a white solid (416 mg, 74%). 1H NMR (CDCl3, 400 MHz): 7.23 (d, J=8.1 Hz, 1H), 7.03 (dd, J=8.1, 1.9 Hz, 1H), 6.95 (d, J=1.9 Hz, 1H), 3.99 (q, J=7.0 Hz, 2H), 3.47 (s, 2H), 2.46-2.35 (m, 4H), 1.61-1.53 (m, 4H), 1.45-1.36 (m, 5H).

Aufarbeitung

  1. customThe reaction mixture was then sonicated for 30 minutes until gas evolution
  2. extractionextracted with DCM (3×30 mL)
  3. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto afford a colourless oil that
  7. customwas then purified by flash chromatography (silica, 12 g column, ISCO, 0-10% methanol in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-dd09fa19466249cbacb188286af2f7b4
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216980B2

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