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

HRID 859925노트

반응식

HRID 859925 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8082Piperidine용매

반응 조건

온도
105 °C

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-ab3e761a5704466c90be9df35e415438
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153857B2

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