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

HRID 6790

반응식

HRID 6790 반응식
[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

참가 물질

7

반응물 2

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

생성물 1

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

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 167845palladium(II) acetate촉매HCID 19696886Tri(o-toluoyl)phosphine촉매HCID 8021Diethylamine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-407eb598551c4c3b88f8f45387ed5837
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084158B2

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