2-(2-Chlorobenzylidene)-1-azabicyclo[2.2.2]octan-3-one → 2-[(2-Chlorophenyl)phenylmethyl]-1-azabicyclo[2.2.2]octan-3-one

HRID 4979

Reaction equation

HRID 4979 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH:4]=[C:5]1[C:10](=[O:11])[CH:9]2[CH2:12][CH2:13][N:6]1[CH2:7][CH2:8]2.[C:18]1([Mg]Br)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH:4]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:5]1[C:10](=[O:11])[CH:9]2[CH2:12][CH2:13][N:6]1[CH2:7][CH2:8]2

Participants

4

Reactant 2

HCID 2974052-(2-Chlorobenzylidene)-1-azabicyclo[2.2.2]octan-3-oneHCID 178418255HCID 178418255, compound

Product 1

HCID 197974782-[(2-Chlorophenyl)phenylmethyl]-1-azabicyclo[2.2.2]octan-3-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

2-(2-Chlorobenzylidene)-1-azabicyclo[2.2.2]octan-3-one (3 g) was dissolved in toluene (30 ml) and placed in a dropping funnel. Phenylmagnesium bromide was dissolved in toluene (15 ml) and stirred under nitrogen. This was cooled in an ice/water bath and the benzylidene solution was added dropwise. After 3 hrs the reaction was quenched with ammonium chloride solution and the aqueous layer extracted with dichloromethane (×4); this was combined with the original toluene layer and dried (MgSO4). The solvent was removed in vacuo and the residue purified by chromatography on silica eluting with 1:1 hexane:diethyl ether which afforded the title compound as a 2:1 mixture of its diastereoisomers:

Workup

  1. customplaced in a dropping funnel
  2. temperatureThis was cooled in an ice/water bath
  3. customAfter 3 hrs the reaction was quenched with ammonium chloride solution
  4. extractionthe aqueous layer extracted with dichloromethane (×4)
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo
  7. customthe residue purified by chromatography on silica eluting with 1:1 hexane

Sources & evidence

ORD record
ord-28e88db65242445cb373f341e46ba373
Source dataset
uspto-grants-1993_09
Patent number
US05242930

Linked notes

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