Methyl Isocyanate → Ethyl 1-(n-methylaminocarbonyl)-4-oxo-3-piperidinecarboxylate

HRID 432797Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 432797
[CH3:1][CH2:2][O:3][C:4]([CH:6]1[C:11](=[O:12])[CH2:10][CH2:9][NH:8][CH2:7]1)=[O:5].Cl.C(N(C(C)C)CC)(C)C.[CH3:23][N:24]=[C:25]=[O:26]>ClCCl>[CH3:23][NH:24][C:25]([N:8]1[CH2:9][CH2:10][C:11](=[O:12])[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7]1)=[O:26]

Komponenten

5

Edukt 3

HCID 12228Methyl IsocyanateHCID 81531DiisopropylethylamineHCID 1073153-Piperidinecarboxylic acid, 4-oxo-, ethyl ester, hydrochloride (1:1)

Produkt 1

HCID 18760282Ethyl 1-(n-methylaminocarbonyl)-4-oxo-3-piperidinecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Commercially available ethyl 4-piperidone-3-carboxylate hydrochloride (203.2 mg; 0.98 mmol) was suspended in dichloromethane (7 ml), diisopropylethylamine (180 μl; 0.99 mmol) was added, followed by commercially available methyl isocyanate and (57 μl; 0.98 mmol). This mixture was stirred at ambient temperature for approximately 3 hours, and then diluted with fresh dichloromethane and washed with water. The dichloromethane solution was dried with anhydrous potassium carbonate and evaporated at ambient temperature under reduced pressure, giving ethyl 1-(N-methylaminocarbonyl)-4-oxo-3-piperidinecarboxylate (74.4 mg) as a white solid. MS m/z (positive ion) 479 (dimer+Na+; 40), 457 (dimer+; 25), 251 (M+Na+; 100), 229 (MH+; 90), 205 (25), 130 (25).

Aufarbeitung

  1. washwashed with water
  2. dry with materialThe dichloromethane solution was dried with anhydrous potassium carbonate
  3. customevaporated at ambient temperature under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5c25927d6f514dd4815de0cb4cd844aa
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06664271B1

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