Phenylacetylene → HCID 13910718, compound

HRID 1252194Notes

Reaction equation

HRID 1252194 reaction equation
[ClH:1].I[C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH2:11][CH:12]([CH3:25])[N:13]([CH3:24])[CH2:14][CH2:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[C:26]1([C:32]#[CH:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(N(CC)CC)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I>[ClH:1].[CH3:10][O:9][C:6]1[CH:7]=[CH:8][C:3]([C:33]#[C:32][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:4]([CH2:11][CH:12]([CH3:25])[N:13]([CH3:24])[CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:5]=1

Participants

6

Reactant 2

HCID 10821PhenylacetyleneHCID 20141149HCID 20141149, compound

Product 1

HCID 13910718HCID 13910718, compoundYield 33.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst2×HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalyst2×HCID 8471TriethylamineSolvent

Procedure

The free base of 2-iodo-5-methoxy-N,alphadimethyl-N-[(phenyl)butyl]benzeneethanamine hydrochloride (1.66 g, 3.1 mmole) was dissolved in 10 ml of triethylamine and 0.68 ml (6.2 mmole) of phenylacetylene, 11 mg (0.015 mmole) of bis(triphenylphosphine) palladium (II) chloride and 6 mg (0.03 mmole) copper (I) iodide were added. The mixture was stirred under argon at room temperature for 20 hours. An additional 6 mg copper (I) iodide and 11 mg bis(triphenylphosphine) palladium (II) chloride were added. The mixture was stirred for 20 hours. The solvent was evaporated in vacuo. The residue was taken up in CH2Cl2. The CH2Cl2 was washed with dilute HCl and dilute NaOH solution, dried (K2CO3) and the solvent evaported in vacuo. A hydrochloride salt was prepared from ethereal hydrogen chloride and recrystallized twice from 2-propanolether to give 0.46 g of 5-methoxy-N,alphadimethyl-N-[(phenyl)butyl]-2-[(phenyl)ethynyl]benzeneethanamine hydrochloride, mp 133°-135° C.

Workup

  1. stirringThe mixture was stirred for 20 hours
  2. customThe solvent was evaporated in vacuo
  3. washThe CH2Cl2 was washed with dilute HCl and dilute NaOH solution
  4. dry with materialdried (K2CO3)
  5. customrecrystallized twice from 2-propanolether

Sources & evidence

ORD record
ord-5ff1b6303ae24123a07febad54a95985
Source dataset
uspto-grants-1988_05
Patent number
US04742084

Reaction notes

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