Potassium Fluoride → N-[(1RS,2RS)-3-(4-chlorophenyl)-1-methyl-2-{4-(3-thienyl)phenyl}propyl]phthalimide

HRID 376184Notes

Reaction equation

HRID 376184 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[CH:9]([N:11]2[C:15](=[O:16])[C:14]3=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]3[C:12]2=[O:21])[CH3:10])=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:35]1[CH:39]=[CH:38][S:37][CH:36]=1)CCC.[F-].[K+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][CH:8]([C:5]2[CH:6]=[CH:7][C:2]([C:35]3[CH:39]=[CH:38][S:37][CH:36]=3)=[CH:3][CH:4]=2)[CH:9]([N:11]2[C:12](=[O:21])[C:13]3=[CH:20][CH:19]=[CH:18][CH:17]=[C:14]3[C:15]2=[O:16])[CH3:10])=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 522689Potassium FluorideHCID 10959689Stannane, tributyl-3-thienyl-HCID 19073589N-{(1RS,2RS)-2-(4-bromophenyl)-3-(4-chlorophenyl)-1-methylpropyl}phthalimide

Product 1

HCID 19073667N-[(1RS,2RS)-3-(4-chlorophenyl)-1-methyl-2-{4-(3-thienyl)phenyl}propyl]phthalimideYield 72.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

113 mg of N-{(1RS, 2RS)-2-(4-bromophenyl)-3-(4-chlorophenyl)-1-methylpropyl}phthalimide prepared in the same manner as in Example 114, was dissolved in 3 ml of toluene, and 99 mg of tributyl(3-thienyl)tin and 14 mg of tetrakis(triphenylphosphine)palladium (0) were added thereto. The mixture was refluxed under heating for 3 hours in a light-shielding nitrogen atmosphere. The reaction solution was left to cool to room temperature. Then, 2 ml of a 5% potassium fluoride aqueous solution was added thereto, and the mixture was stirred for 30 minutes. Insoluble matters were separated by filtration. Then, ethyl acetate and water were added to the filtrate for liquid separation. The organic layer was collected by separation, washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The drying agent was separated by filtration, and then the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (hexane/ethyl acetate=100/1→30/1) to obtain 83 mg of N-[(1RS, 2RS)-3-(4-chlorophenyl)-1-methyl-2-{4-(3-thienyl)phenyl}propyl]phthalimide

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 3 hours in a light-shielding nitrogen atmosphere
  3. waitThe reaction solution was left
  4. customInsoluble matters were separated by filtration
  5. additionThen, ethyl acetate and water were added to the filtrate for liquid separation
  6. customThe organic layer was collected by separation
  7. washwashed with a saturated sodium chloride aqueous solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe drying agent was separated by filtration
  10. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-89b8b33818b642c7bd0d3d1805de4067
Source dataset
uspto-grants-1996_01
Patent number
US05488149

Reaction notes

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