Trimethylsilylacetylene → N-{4-Methoxy-3-[(trimethylsilyl)ethynyl]phenyl}-1-methylpiperidin-4-amine

HRID 1403212노트

반응식

HRID 1403212 반응식
I[C:2]1[CH:3]=[C:4]([NH:10][CH:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[C:18]([Si:20]([CH3:23])([CH3:22])[CH3:21])#[CH:19]>C(#N)C.O1CCOCC1.[Cu]I>[CH3:9][O:8][C:7]1[CH:6]=[CH:5][C:4]([NH:10][CH:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)=[CH:3][C:2]=1[C:19]#[C:18][Si:20]([CH3:23])([CH3:22])[CH3:21]

참가 물질

6

반응물 2

HCID 66111TrimethylsilylacetyleneHCID 71240893N-(3-iodo-4-methoxyphenyl)-1-methylpiperidin-4-amine

생성물 1

HCID 86725293N-{4-Methoxy-3-[(trimethylsilyl)ethynyl]phenyl}-1-methylpiperidin-4-amine

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6342Acetonitrile용매HCID 312751,4-Dioxane용매

실험 절차

Into a flask maintained under argon atmosphere N-(3-iodo-4-methoxyphenyl)-1-methylpiperidin-4-amine (180 mg, 0.52 mmol), CuI (9.9 mg, 0.052 mmol) and Pd(Ph3P)Cl2 (36.5 mg, 0.052 mmol) were added and dissolved in acetonitrile (5 mL) and dioxane (5 mL). The solution was degassed and backfilled with argon for three times. TEA (0.725 mL, 526 mg, 5.2 mmol) and (ethynyl)trimethylsilane (0.147 mL, 0.102 mg, 1.04 mmol) were added with a syringe and the solution was stirred at room temperature for 75 min. The volatiles were evaporated and the residue was taken up with EtOAc (30 mL), washed with water (3×5 mL), dried over sodium sulfate and the solvent was removed under vacuum.

후처리

  1. additionwere added
  2. customThe solution was degassed
  3. customThe volatiles were evaporated
  4. washwashed with water (3×5 mL)
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was removed under vacuum

출처 및 근거

ORD 기록
ord-e298d8c2e8db488bb5e1bf49a4bd992c
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912200B2

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