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3-Bromobenzoic acid → HCID 23599468, compound

HRID 1350887
Notes
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Reaction equation

HRID 1350887 reaction equation
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:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16](O)=[O:17]>>[N:3]12[CH2:10][CH2:9][CH:6]([CH2:7][CH2:8]1)[C@@H:5]([NH:11][C:16](=[O:17])[C:15]1[CH:19]=[CH:20][CH:21]=[C:13]([Br:12])[CH:14]=1)[CH2:4]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 114563-Bromobenzoic acidHCID 12494972(R)-(+)-3-Aminoquinuclidine Dihydrochloride

Product 1

HCID 23599468HCID 23599468, compound

Procedure

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 3-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/diethyl ether to give the hydrochloride salt of the title compound as a colourless solid; MS (ES+) 309, 311 (MH+).

Workup

  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
  • dissolutionThe compound was then dissolved in tetrahydrofuran
  • additionexcess hydrogen chloride (1M solution in diethyl ether) was added
  • customthe solution was evaporated
  • customrecrystallised from methanol/diethyl ether
  • Sources & evidence

    ORD record
    ord-5d075c9cf6ed41d7ab85adb2114f3f8b
    Source dataset
    uspto-grants-2007_05
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US07214688B2

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes