Water → 2-[(Ethyl-pyridin-4-ylmethyl-amino)-methyl]-1-aza-bicyclo[2.2.2]octan-3-one

HRID 2356375

Reaktionsgleichung

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([N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:3]([N:4]([CH2:2][CH:3]1[C:8](=[O:9])[CH:7]2[CH2:10][CH2:11][N:4]1[CH2:5][CH2:6]2)[CH2:5][C:6]1[CH:17]=[CH:16][N:15]=[CH:18][CH:19]=1)[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a stirred solution of 2-methylene-3-quinuclidinone hydrochloride (0.5 g, 0.0036 mol) in water (3 ml) N-(4-pyridylmethyl)ethylamine (0.49 g, 0.0036 mol), triethylamine (1.09 g, 0.0108 mol) and tetra-n-butyl ammonium bromide (116 mg, 0.00036 mol) were added and the reaction mixture were 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 (10 ml), extracted with dichloromethane (2×50 ml), organic layers were washed with 10% NaHCO3 solution, brine and dried over sodium sulphate, filtered and concentrated to get the crude product which was purified as yellow solids (200 mg, 22%) by flash column chromatography on neutral silica gel using chloroform as eluent.

Aufarbeitung

customThe completion of reaction
customThe reaction mixture was quenched with ice-cold water (10 ml)
extractionextracted with dichloromethane (2×50 ml), organic layers
washwere washed with 10% NaHCO3 solution, brine
dry with materialdried over sodium sulphate
filtrationfiltered
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-e5a1120a58cc4d9687d2bd7ad3177757
Quelldatensatz: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07759361B2

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