Ethanol → 1-(4-(3-(4-Methoxyphenyl)cinnamoylamino)benzyl)piperidine

HRID 2228116Notes

Reaction equation

HRID 2228116 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[CH:5]=[CH:6][C:7]([NH:9][C:10]1[CH:22]=[CH:21][C:13]([CH2:14][N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:12][CH:11]=1)=[O:8].B([O-])([O-])O[C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+].C(O)C>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>[CH3:35][O:34][C:31]1[CH:32]=[CH:33][C:28]([C:2]2[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=2)[CH:5]=[CH:6][C:7]([NH:9][C:10]2[CH:22]=[CH:21][C:13]([CH2:14][N:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[CH:12][CH:11]=2)=[O:8])=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 539077661-(4-(3-Bromocinnamoylamino)benzyl)piperidineHCID 86645335(4-Methoxyphenyl)borate

Product 1

HCID 541118661-(4-(3-(4-Methoxyphenyl)cinnamoylamino)benzyl)piperidineYield 105.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A suspension of 1—(4—(3-bromocinnamoylamino)benzyl)piperidine (0.4 g), 4-methoxyphenyl borate (0.14 g), 1M potassium carbonate (2 ml) and ethanol (1 ml) in toluene (5 ml) was stirred under argon atmosphere at room temperature for 30 minutes. To the suspension was added tetrakistriphenylphosphinepalladium (0.05 g), and the mixture was refluxed over night. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated sodium chloride solution, and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column (methanol/triethylamine/ethyl acetate) to give crude crystals, which were recrystallized from ethyl acetate-hexane to give 1—(4—(3—(4-methoxyphenyl)cinnamoylamino)benzyl)piperidine (Compound 84) (0.38 g) as colorless crystals.

Workup

  1. temperaturethe mixture was refluxed over night
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with water and saturated sodium chloride solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customUnder reduced pressure, the solvent was evaporated
  6. customthe residue was purified with silica gel column (methanol/triethylamine/ethyl acetate)
  7. customto give crude crystals, which
  8. customwere recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-74672dceb6d1496f99433d25fe8aa5a7
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

Loading…