Iodobenzene → N-BOC-4-(phenylethynyl)piperidine

HRID 899349Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 899349
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]#[CH:15])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].I[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(N(CC)CC)C.[Cu]I>[C:1]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]#[C:15][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][CH2:13]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Komponenten

5

Edukt 2

HCID 11575IodobenzeneHCID 15550481tert-Butyl 4-ethynylpiperidine-1-carboxylate

Produkt 1

HCID 17986993N-BOC-4-(phenylethynyl)piperidineAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
82 °C

Versuchsvorschrift

N-BOC4-ethynylpiperidin, 0.5 g (2.40 mmol), and iodobenzene, 0.29 mL (2.64 mmol) were dissolved in triethylamine (9 mL) and argon was passed through for a few minutes. Copper(I) iodide, 0.087 g (0.5 mmol), and bis[triphenylphosphine]palladium dichloride, 0.070 g (0.1 mmol), were added and the mixture was heated to 82° C. in a closed vessel for 17 hours. TLC analysis indicated complete reaction. Triethylamine was evaporated and the mixture was purified by silica gel chromatography (75 mL) using heptane/ethyl acetate (4+1) as eluant. Evaporation of pure fractions gave 0.497 g (73%) of N-BOC4-(phenylethynyl)piperidine. The protected piperidine, 0.497 g (1.74 mmol), was dissolved in dichloromethane and trifluoroacetic acid (1 mL) was added. The reaction was completed within 20 hours and the mixture was evaporated to give an oil. NMR analysis showed pure ammonium trifluoroacetate, contaminated with trifluoroacetic acid. The product was dissolved in dichloromethane and extracted with aqueous sodium hydrogen carbonate and water. Evaporation of solvent gave 0.284 g (88%) of the sub-titled compound.

Aufarbeitung

  1. customwas passed through for a few minutes
  2. customreaction
  3. customTriethylamine was evaporated
  4. customthe mixture was purified by silica gel chromatography (75 mL)
  5. customEvaporation of pure fractions

Quellen und Nachweise

ORD-Eintrag
ord-4c39675851264a0e89710ca1aabaadb8
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07354940B2

Notizen zur Reaktion

Wird geladen…