Phenylacetylene → HCID 69606755, compound

HRID 859923Notes

Reaction equation

HRID 859923 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14](Br)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)(=[O:4])=[O:3].[C:18]1([C:24]#[CH:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>N1CCCCC1.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([C:25]#[C:24][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)(=[O:4])=[O:3]

Participants

7

Reactant 2

HCID 10821PhenylacetyleneHCID 219193841-(4-Bromophenyl)-4-(methylsulfonyl)piperazine

Product 1

HCID 69606755HCID 69606755, compoundYield 32.4%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8082PiperidineSolvent

Conditions

Temperature
105 °C

Procedure

To a stirred suspension of 1-(methylsulfonyl)-4-(4-bromophenyl)piperazine (5.77 g, 18.1 mmol), phenyl acetylene (3.97 mL, 36.1 mmol), Copper (I) iodide (38 mg, 0.2 mmol) and triphenylphosphine (95 mg, 0.36 mmol) in piperidine (72 mL) at 20° C. was added dichlorobis(triphenylphosphine)palladium(II) (38 mg, 54 mmol). The reaction was warmed to 105° C. and stirred for 14 hours under an inert atmosphere. Volatiles were removed in vacuo, and the solid residue was dissolved in CH2Cl2 (200 mL) and washed with aqueous hydrochloric acid (2M) to pH 2. The layers were then separated and the organic extract dried, (sat. Brine and MgSO4), filtered and evaporated to dryness in vacuo. The residue was triturated in CH2Cl2, and filtered to give 1-(methylsulfonyl)-4-[4-(phenylethynyl)phenyl]piperazine as a flaky white solid (1.99 g, 5.86 mmol, 32%).

Workup

  1. customVolatiles were removed in vacuo
  2. dissolutionthe solid residue was dissolved in CH2Cl2 (200 mL)
  3. washwashed with aqueous hydrochloric acid (2M) to pH 2
  4. customThe layers were then separated
  5. extractionthe organic extract
  6. dry with materialdried, (sat. Brine and MgSO4),
  7. filtrationfiltered
  8. customevaporated to dryness in vacuo
  9. customThe residue was triturated in CH2Cl2
  10. filtrationfiltered

Sources & evidence

ORD record
ord-392923178bdb4f829c70050a70c85f88
Source dataset
uspto-grants-2006_12
Patent number
US07153857B2

Reaction notes

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