3,4-Dichlorocinnamic acid → (R)-N-(1-Azabicyclo[2.2.2]oct-3-yl)-[E-3-(3,4-dichlorophenyl)propenamide]

HRID 1840903

Reaction equation

HRID 1840903 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.[Cl:12][C:13]1[CH:14]=[C:15](/[CH:20]=[CH:21]/[C:22](O)=[O:23])[CH:16]=[CH:17][C:18]=1[Cl:19]>>[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:15]1[CH:16]=[CH:17][C:18]([Cl:19])=[C:13]([Cl:12])[CH:14]=1)[CH2:4]2

Participants

3

Reactant 2

HCID 6880273,4-Dichlorocinnamic acidHCID 12494972(R)-(+)-3-Aminoquinuclidine Dihydrochloride

Product 1

HCID 20613755(R)-N-(1-Azabicyclo[2.2.2]oct-3-yl)-[E-3-(3,4-dichlorophenyl)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-(3,4-dichlorophenyl)propenoic acid; the compound was purified by chromatography on silica gel using ammoniated methanol/chloroform mixtures as the eluent; MS (ES+) 325, 327, 329 (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-5c397db0794948f394faaf52ce40f4dd
Source dataset
uspto-grants-2004_01
Patent number
US06683090B1

Linked notes

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