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

HRID 6790

Reaction equation

HRID 6790 reaction equation
[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

Participants

7

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 167845palladium(II) acetateCatalystHCID 19696886Tri(o-toluoyl)phosphineCatalystHCID 8021DiethylamineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-407eb598551c4c3b88f8f45387ed5837
Source dataset
uspto-grants-2006_08
Patent number
US07084158B2

Linked notes

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