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

HRID 1403212Notes

Reaction equation

HRID 1403212 reaction equation
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]

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e298d8c2e8db488bb5e1bf49a4bd992c
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

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