1-Fluoro-3-iodobenzene → 1-[3-(3-Fluorophenyl)-2-propynyl]4-methylpiperidine

HRID 6790

反応式

HRID 6790 の反応式
[F:1][C:2]1[CH:3]=[C:4](I)[CH:5]=[CH:6][CH:7]=1.[CH3:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]#[CH:18])[CH2:12][CH2:11]1>C(NCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Cu]I.C1(C)C(C(P(C(C2C(C)=CC=CC=2)=O)C(C2C(C)=CC=CC=2)=O)=O)=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([C:18]#[C:17][CH2:16][N:13]2[CH2:14][CH2:15][CH:10]([CH3:9])[CH2:11][CH2:12]2)[CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 2

HCID 707251-Fluoro-3-iodobenzeneHCID 113555094-Methyl-1-(prop-2-yn-1-yl)piperidine

生成物 1

HCID 98994381-[3-(3-Fluorophenyl)-2-propynyl]4-methylpiperidine収率 56.2%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 167845palladium(II) acetate触媒HCID 19696886Tri(o-toluoyl)phosphine触媒HCID 8021Diethylamine溶媒

実験手順

A mixture of 3-fluoroiodobenzene (8.88 g), 4-methyl-1-(2-propynyl)piperidine (6.80 g), palladium acetate (0.045 g), tri-o-toloylphosphine (0.24 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 the solvent was removed under reduced pressure. Distillation of the residue under reduced pressure gave an oil (5.20 g) of boiling point 105° C./0.07 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. customthe solvent was removed under reduced pressure
  7. distillationDistillation of the residue under reduced pressure

出典と根拠

ORDレコード
ord-407eb598551c4c3b88f8f45387ed5837
出典データセット
uspto-grants-2006_08
特許番号
US07084158B2

関連ノート

読み込み中…