Dimethyl Sulfoxide → HCID 67455735, compound

HRID 2368780Notes

Reaction equation

HRID 2368780 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C@@H:7]([N:11]1[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]1)[CH2:6][CH2:5]2.CS(C)=[O:20].N#N.C1(P([C:47]2[CH:52]=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:53]([OH:55])C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C>[CH3:17][N:14]1[CH2:15][CH2:16][N:11]([C@@H:7]2[C:8]3[C:4](=[CH:3][C:2]([C:53]([O:55][CH2:52][CH3:47])=[O:20])=[CH:10][CH:9]=3)[CH2:5][CH2:6]2)[CH2:12][CH2:13]1

Participants

8

Reactant 5

HCID 679Dimethyl SulfoxideHCID 702EthanolHCID 947Nitrogen2×HCID 812191,3-Bis(diphenylphosphino)propaneHCID 67456730HCID 67456730, compound

Product 1

HCID 67455735HCID 67455735, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
90 °C

Procedure

1-((1S)-5-Bromo-2,3-dihydro-1H-inden-1-yl)-4-methylpiperazine (29.6 g, 100 mmol) was dissolved in 300 mL of ethanol, 30 mL of DMSO and 42 mL of triethylamine. The system was vacuumized and charged with N2. After palladium acetate (2.4 g, 10 mmol) and 1,3-bis(diphenylphosphino)propane (3.3 g, 10 mmol) were added, the system was vacuumized and charged with N2. After being vacuumized once again, the mixture was stirred at 90° C. for 2 days under CO. After being cooled to the room temperature, the solution was filtered by kieselguhr and then concentrated. The residue was dissolved in ethyl acetate (500 mL) and the solution obtained was washed with brine (3×200 mL), dried over magnesium sulfate, concentrated, and finally separated by silica gel column chromatography using 50% ethyl acetate/45% methylene chloride/5% triethylamine as the eluent to obtain 17.3 g of the title compound (60% yield). MS (M+1)=289.18.

Workup

  1. temperatureAfter being cooled to the room temperature
  2. filtrationthe solution was filtered by kieselguhr
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in ethyl acetate (500 mL)
  5. customthe solution obtained
  6. washwas washed with brine (3×200 mL)
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customfinally separated by silica gel column chromatography

Sources & evidence

ORD record
ord-b4b76697db7040a2b5d0cb46d7114400
Source dataset
uspto-grants-2014_04
Patent number
US08703771B2

Reaction notes

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