Triphenylphosphine → 1-(Methylsulfonyl)-4-[4-(trimethylsilylethynyl)phenyl]piperazine

HRID 859925Notes

Reaction equation

HRID 859925 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].[CH3:18][Si:19]([C:22]#[CH:23])([CH3:21])[CH3:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=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>[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([C:23]#[C:22][Si:19]([CH3:21])([CH3:20])[CH3:18])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)(=[O:4])=[O:3]

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 219193841-(4-Bromophenyl)-4-(methylsulfonyl)piperazine

Product 1

HCID 696067501-(Methylsulfonyl)-4-[4-(trimethylsilylethynyl)phenyl]piperazine

Reagents, catalysts & solvents 3

HCID 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 (4.79 g, 15 mmol, prepared as in example 3), trimethylsilylacetylene (4.15 mL, 30 mmol), Copper (I) iodide (31 mg, 0.17 mmol) and triphenylphosphine (80 mg, 0.3 mmol) in piperidine (60 mL) at 20° C. was added dichlorobis(triphenylphosphine)palladium(II) (31 mg, 45 μmol). The reaction was warmed to 105° C. and stirred for 8 hours under an inert atmosphere. After cooling, the suspension was filtered and washed with toluene. The solid was dissolved in CH2Cl2, washed with water and filtered through silica, washing with CH2Cl2. The filtrate was concentrated and the resulting suspension filtered, washing well with CH2Cl2/iHexane to give 1-(methylsulfonyl)-4-[4-(trimethylsilylethynyl)phenyl]piperazine as a white powder (3.05 g, 9.06 mmol, 60

Workup

  1. temperatureAfter cooling
  2. filtrationthe suspension was filtered
  3. washwashed with toluene
  4. dissolutionThe solid was dissolved in CH2Cl2
  5. washwashed with water
  6. filtrationfiltered through silica
  7. washwashing with CH2Cl2
  8. concentrationThe filtrate was concentrated
  9. filtrationthe resulting suspension filtered
  10. washwashing well with CH2Cl2/iHexane

Sources & evidence

ORD record
ord-ab3e761a5704466c90be9df35e415438
Source dataset
uspto-grants-2006_12
Patent number
US07153857B2

Reaction notes

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