HCID 54565072, compound → HCID 19967097, compound

HRID 976285Notes

Reaction equation

HRID 976285 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:23]=[CH:22][C:11]([CH:12]=[C:13]3[C:18](=[O:19])[CH:17]4[CH2:20][CH2:21][N:14]3[CH2:15][CH2:16]4)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1>C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH2:12][CH:13]3[C:18](=[O:19])[CH:17]4[CH2:20][CH2:21][N:14]3[CH2:15][CH2:16]4)=[CH:22][CH:23]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 54565072HCID 54565072, compound

Product 1

HCID 19967097HCID 19967097, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-[4-(4-fluorophenyl)benzylidene]quinuclidin-3-one (1.3 g) in ethyl acetate (40 ml) was hydrogenated at atmospheric pressure for 4 hours over a catalyst of 10% palladium on carbon. The catalyst was removed by filtration and the filtrate evaporated. The residue was purified by medium pressure chromatography on silica gel using ethyl acetate as eluant to give 2-[4-(4-fluorophenyl)benzyl]quinuclidin-3-one as a colourless solid (38% yield), m.p. 122°-123° C., microanalysis, found: C, 77.5; H, 6.5; N, 4.4% C20H20FNO requires: C, 77.6; H, 6.5; N, 4.5%; NMR (CDCl3): 1.9-2.1 (4H, m), 2.5 (1H, m), 2.8-3.0 (3H, m), 3.1-3.3 (3H, m), 3.4 (1H, d of d), 7.1 (2H, m), 7.3-7.4 (2H, d) and 7.4-7.6 (4H, m); m/z 310 (M+H).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate evaporated
  3. customThe residue was purified by medium pressure chromatography on silica gel

Sources & evidence

ORD record
ord-216f70321f284d138473e53a70845fd4
Source dataset
uspto-grants-1997_03
Patent number
US05612352

Reaction notes

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