Water → HCID 11379632, Verbindung

HRID 2356378

Reaktionsgleichung

Reaktionsgleichung von HRID 2356378
Cl.[CH2:2]=[C:3]1[C:8](=[O:9])[CH:7]2[CH2:10][CH2:11][N:4]1[CH2:5][CH2:6]2.O.[C:13]1([SH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:13]1([S:19][CH2:2][CH:3]2[C:8](=[O:9])[CH:7]3[CH2:10][CH2:11][N:4]2[CH2:5][CH2:6]3)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 7969ThiophenolHCID 184012841-Azabicyclo(2.2.2)octan-3-one, 2-methylene-, hydrochloride (1:1)

Produkt 1

HCID 11379632HCID 11379632, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 74236Tetrabutylammonium BromideKatalysator

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirred solution of 2-methylene-3-quinuclidinone hydrochloride (1 g, 0.0057 mol) in water (10 ml) triethylamine (1.73 g, 0.0171 mol), tetra-n-butyl ammonium bromide (180 mg, 0.00057 mol) and thiophenol (0.63 g, 0.0057 mol) were added and the reaction mixture was allowed to stir at 80° C. for 18 h. The completion of reaction was monitored by tlc. The reaction mixture was quenched with ice-cold water (20 ml), extracted with dichloromethane (4×50 ml), organic layers were washed with brine and dried over sodium sulphate, filtered and concentrated to get the crude product which was purified (550 mg) by column chromatography on silica gel using chloroform as eluent.

Aufarbeitung

  1. customThe completion of reaction
  2. customThe reaction mixture was quenched with ice-cold water (20 ml)
  3. extractionextracted with dichloromethane (4×50 ml), organic layers
  4. washwere washed with brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9d07993715534551b8d96edf27dfb81b
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07759361B2

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