1-(p-Tolyl)piperazine → HCID 59485072, compound

HRID 2063915Notes

Reaction equation

HRID 2063915 reaction equation
Br[C:2]1[C:3]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)=[C:4]([CH3:13])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH2:7][C:6]=2[CH:12]=1.[CH3:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[CH:24][CH:23]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CC(C)([O-])C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH3:10][C:8]1([CH3:11])[CH2:7][C:6]2[CH:12]=[C:2]([N:31]3[CH2:32][CH2:33][N:28]([C:25]4[CH:26]=[CH:27][C:22]([CH3:21])=[CH:23][CH:24]=4)[CH2:29][CH2:30]3)[C:3]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)=[C:4]([CH3:13])[C:5]=2[O:9]1

Participants

7

Reactant 4

HCID 831131-(p-Tolyl)piperazineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 66759547HCID 66759547, compound

Product 1

HCID 59485072HCID 59485072, compoundYield 3.1%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

To a solution of toluene (10 mL) containing 5-bromo-2,2,7-trimethyl-6-(4-methylphenyl)-2,3-dihydro-1-benzofuran (300 mg, 0.910 mmol) synthesized in Reference Example 157, 1-(4-methylphenyl)piperazine (160 mg, 0.910 mmol), Tris(dibenzylideneacetone)dipalladium (0) (24.9 mg, 0.027 mmol) and Xantphos (47.2 mg, 0.082 mmol), sodium tert-butoxide (131 mg, 1.36 mmol) was added, and the mixture was stirred under heated reflux for 15 hours. After cooled to room temperature, the reaction solution was subjected to Celite filtration. Water was added to the filtration, and extraction was performed using ethyl acetate. The extract was dried using anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. After that, the residue was purified by silica gel chromatography (hexane-ethyl acetate 10:1), and it was crystallized from acetonitrile to obtain 12.0 mg of the title compound as a white solid (yield 3%).

Workup

  1. additionwas added
  2. temperatureunder heated
  3. temperaturereflux for 15 hours
  4. filtrationthe reaction solution was subjected to Celite filtration
  5. additionWater was added to the filtration, and extraction
  6. customThe extract was dried
  7. customthe solvent was removed under reduced pressure
  8. customAfter that, the residue was purified by silica gel chromatography (hexane-ethyl acetate 10:1), and it
  9. customwas crystallized from acetonitrile

Sources & evidence

ORD record
ord-d364dfb08ea84b52ab752dd414927353
Source dataset
uspto-grants-2012_10
Patent number
US08288390B2

Reaction notes

Loading…