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

HRID 859925ノート

反応式

HRID 859925 の反応式
[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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 8082Piperidine溶媒

反応条件

温度
105 °C

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-ab3e761a5704466c90be9df35e415438
出典データセット
uspto-grants-2006_12
特許番号
US07153857B2

反応ノート

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