4-Iodobenzoic acid → HCID 11187399, compound

HRID 891436Notes

Reaction equation

HRID 891436 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.[I: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]([I:12])=[CH:14][CH:15]=1)[CH2:4]2

Participants

3

Reactant 2

HCID 120854-Iodobenzoic acidHCID 12494972(R)-(+)-3-Aminoquinuclidine Dihydrochloride

Product 1

HCID 11187399HCID 11187399, 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 4-iodobenzoic acid; the compound was purified by solid phase extraction on silica gel using ammoniated methanol/chloroform mixtures as the eluent followed by reverse phase HPLC on a Waters Bondapak® C18 column using a gradient of acetonitrile and 0.1% aqueous trifluoroacetic acid as the eluent. The product-containing fractions were evaporated, the residue was dissolved in methanol, excess hydrogen chloride solution (4M in 1,4-dioxane) was added and the solution was evaporated to give the hydrochloride salt of the title compound as a colourless solid; MS (ES+) 357 (MH+).

Workup

  1. customPrepared by a method analogous to
  2. customthe compound was purified by solid phase extraction on silica gel using ammoniated methanol/chloroform mixtures as the eluent
  3. customThe product-containing fractions were evaporated
  4. dissolutionthe residue was dissolved in methanol
  5. additionexcess hydrogen chloride solution (4M in 1,4-dioxane) was added
  6. customthe solution was evaporated

Sources & evidence

ORD record
ord-09fb3130f49748f1a879b67a09e07fc8
Source dataset
uspto-grants-2006_02
Patent number
US07001914B2

Reaction notes

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