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

HRID 899349노트

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HRID 899349 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8471Triethylamine용매

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온도
82 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4c39675851264a0e89710ca1aabaadb8
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07354940B2

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