4-Chlorophenyl isothiocyanate → Ethyl 1-{[(4-chlorophenyl)amino]carbonothioyl}-4-methylpiperidine-4-carboxylate

HRID 20276

Reaktionsgleichung

Reaktionsgleichung von HRID 20276
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[S:10])=[CH:4][CH:3]=1.[CH3:11][C:12]1([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([N:15]2[CH2:16][CH2:17][C:12]([CH3:11])([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:13][CH2:14]2)=[S:10])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 164804-Chlorophenyl isothiocyanateHCID 19361805Ethyl 4-methylpiperidine-4-carboxylate

Produkt 1

HCID 59619551Ethyl 1-{[(4-chlorophenyl)amino]carbonothioyl}-4-methylpiperidine-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 4-chlorophenyl isothiocyanate (2.36 g, 13.98 mmol), and ethyl 4-methylpiperidine-4-carboxylate (U.S. 2002/0086887, example 532C) (2.17 g, 12.71 mmol) in dichloromethane (50 mL) was stirred at room temperature for 30 minutes. The mixture was partitioned between dichloromethane and brine, and the layers were separated. The organic phase was dried over MgSO4 and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using dichloromethane:ethyl acetate (100:0 to 90:10) to provide the title compound as a white solid, 3.46 g.

Aufarbeitung

  1. customThe mixture was partitioned between dichloromethane and brine
  2. customthe layers were separated
  3. dry with materialThe organic phase was dried over MgSO4
  4. customevaporated under reduced pressure
  5. customThe crude product was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-0fb11775f62b47738fcab9cbb4c48873
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745630B2

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