4-Bromobenzoic acid → N-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-4-bromobenzamide

HRID 1726335Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1726335
Cl.Cl.[N:3]12[CH2:10][CH2:9][CH:6]([CH2:7][CH2:8]1)[C@@H:5]([NH2:11])[CH2:4]2.[Br:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=1>>[N:3]12[CH2:10][CH2:9][CH:6]([CH2:7][CH2:8]1)[C@@H:5]([NH:11][C:17](=[O:18])[C:16]1[CH:20]=[CH:21][C:13]([Br:12])=[CH:14][CH:15]=1)[CH2:4]2

Komponenten

3

Edukt 2

HCID 114644-Bromobenzoic acidHCID 12494972(R)-(+)-3-Aminoquinuclidine Dihydrochloride

Produkt 1

HCID 11461014N-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-4-bromobenzamide

Versuchsvorschrift

Prepared by a method analogous to that described for the preparation of Intermediate 1 from (R)-1-azabicyclo[2.2.2]oct-3-ylamine dihydrochloride and 4-bromobenzoic acid; the compound was purified by chromatography on silica gel using ammoniated methanol/chloroform mixtures as the eluent. The compound was then dissolved in tetrahydrofuran, excess hydrogen chloride (1M solution in diethyl ether) was added, and the solution was evaporated and then recrystallised from methanol/t-butyl methyl ether to give the hydrochloride salt of the title compound as a colourless solid; MS (ES+) 309, 311 (MH+).

Aufarbeitung

  1. customPrepared by a method analogous to
  2. customthe compound was purified by chromatography on silica gel using ammoniated methanol/chloroform mixtures as the eluent
  3. dissolutionThe compound was then dissolved in tetrahydrofuran
  4. additionexcess hydrogen chloride (1M solution in diethyl ether) was added
  5. customthe solution was evaporated
  6. customrecrystallised from methanol/t-butyl methyl ether

Quellen und Nachweise

ORD-Eintrag
ord-c391c69198404aafa389b5b97a743a09
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07491734B2

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