3-Bromobenzoic acid → HCID 23599468, compound

HRID 891433Notes

Reaction equation

HRID 891433 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

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
  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/diethyl ether

Sources & evidence

ORD record
ord-3efcf02470b040dfbcad545353fb9a65
Source dataset
uspto-grants-2006_02
Patent number
US07001914B2

Reaction notes

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