2-Iodotoluene → 1-(3-o-Tolyl-2-propynyl)piperidine

HRID 6788

反応式

HRID 6788 の反応式
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8].[CH2:9]([N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[C:10]#[CH:11]>C(NCC)C.Cl[Pd-2](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.[Cu]I>[C:3]1([CH3:8])[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:11]#[C:10][CH2:9][N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

参加物

6

反応物 2

HCID 51282-IodotolueneHCID 3366521-(Prop-2-yn-1-yl)piperidine

生成物 1

HCID 120567831-(3-o-Tolyl-2-propynyl)piperidine収率 62.3%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418903HCID 178418903、化合物触媒HCID 8021Diethylamine溶媒

実験手順

A mixture of 2-iodotoluene (6.54 g), N-(2-propynyl)piperidine (3.69 g), dichlorobis(triphenylphosphino)palladium(II) (0.05 g) and copper(I) iodide (0.1 g) in dry diethylamine (50 ml) was heated under reflux for 5 hours. The solvent was removed under reduced pressure and the residue was taken up in diethyl ether and washed with water. The organic phase was dried over magnesium sulfate and concentrated completely under reduced pressure. Distillation of the residue under reduced pressure gave 3.98 g of an oil of boiling point 96–98° C./0.08 mm Hg.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. customThe solvent was removed under reduced pressure
  4. washwashed with water
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. concentrationconcentrated completely under reduced pressure
  7. distillationDistillation of the residue under reduced pressure

出典と根拠

ORDレコード
ord-0f8d0671097c4c1fb7b5e5e1778ceb8b
出典データセット
uspto-grants-2006_08
特許番号
US07084158B2

関連ノート

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