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

HRID 1403212ノート

反応式

HRID 1403212 の反応式
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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6342Acetonitrile溶媒HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e298d8c2e8db488bb5e1bf49a4bd992c
出典データセット
uspto-grants-2014_12
特許番号
US08912200B2

反応ノート

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