m-(Trifluoromethyl)cinnamic acid → (R)-N-(1-Azabicyclo[2.2.2]oct-3-yl)-[E-3-(3-trifluoromethylphenyl)propenamide]

HRID 1840908Notes

Reaction equation

HRID 1840908 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.[F:12][C:13]([F:26])([F:25])[C:14]1[CH:15]=[C:16](/[CH:20]=[CH:21]/[C:22](O)=[O:23])[CH:17]=[CH:18][CH:19]=1>>[N:3]12[CH2:10][CH2:9][CH:6]([CH2:7][CH2:8]1)[C@@H:5]([NH:11][C:22](=[O:23])/[CH:21]=[CH:20]/[C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([C:13]([F:25])([F:26])[F:12])[CH:15]=1)[CH2:4]2

Participants

3

Reactant 2

HCID 719451m-(Trifluoromethyl)cinnamic acidHCID 12494972(R)-(+)-3-Aminoquinuclidine Dihydrochloride

Product 1

HCID 20613760(R)-N-(1-Azabicyclo[2.2.2]oct-3-yl)-[E-3-(3-trifluoromethylphenyl)propenamide]

Procedure

Prepared as a free base by a method analogous to that described in Example 1 from (R)-1-azabicyclo[2.2.2]oct-3-ylamine dihydrochloride and E-3-(3-trifluoromethylphenyl)propenoic acid; the compound was purified by chromatography on silica gel using ammoniated methanol/chloroform mixtures as the eluent; MS (ES+) 271 (MH+).

Workup

  1. customPrepared as a free base by a method analogous to
  2. customthe compound was purified by chromatography on silica gel using ammoniated methanol/chloroform mixtures as the eluent

Sources & evidence

ORD record
ord-69cfc1ea33cd47e19872f121b55e28ab
Source dataset
uspto-grants-2004_01
Patent number
US06683090B1

Reaction notes

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