Water → HCID 4373472, Verbindung

HRID 646846

Reaktionsgleichung

Reaktionsgleichung von HRID 646846
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:14]([O-:16])=[O:15])=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:7]=1.[NH:17]1[CH2:22][CH2:21]S[CH2:19][CH2:18]1.[OH2:23]>>[N+:14]([C:5]1[CH:4]=[CH:3][C:2]([N:17]2[CH2:22][CH2:21][O:23][CH2:19][CH2:18]2)=[CH:7][C:6]=1[N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)([O-:16])=[O:15]

Komponenten

4

Edukt 3

HCID 962WaterHCID 67164ThiomorpholineHCID 30960791-(5-Chloro-2-nitrophenyl)piperidine

Produkt 1

HCID 4373472HCID 4373472, VerbindungAusbeute 66 %

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of 172 mg (0.715 mmol) 1-(5-chloro-2-nitro-phenyl)-piperidine (as prepared in Example 4, step (a)) and 360 μL (3.58 mmol) of thiomorpholine were heated with stirring under Ar at 140° C. for 40 h. After cooling to RT, the mixture was poured into water (50 mL) and extracted with EtOAc (2×20 mL). The combined extracts were washed with water (3×50 mL) and brine (50 mL) and then dried (Na2SO4). Concentration and chromatography on a 10-g silica SPE column with 60% dichloromethane-hexane afforded 145 mg (66%) of the title compound as a yellow resin: Mass spectrum (ESI, m/z): Calcd. for C15H21N3O2S, 308.1 (M+H), found 308.1.

Aufarbeitung

  1. temperaturewere heated
  2. temperatureAfter cooling to RT
  3. extractionextracted with EtOAc (2×20 mL)
  4. washThe combined extracts were washed with water (3×50 mL) and brine (50 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationConcentration and chromatography on a 10-g silica SPE column with 60% dichloromethane-hexane

Quellen und Nachweise

ORD-Eintrag
ord-f3b5db19c1274465b5cb652ebac8fd66
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07705042B2

Verknüpfte Notizen

Wird geladen…