Phenylacetylene → HCID 13910718, compound

HRID 543435Notes

Reaction equation

HRID 543435 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.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[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 evaporated 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. customthe solvent evaporated in vacuo
  6. customrecrystallized twice from 2-propanolether

Sources & evidence

ORD record
ord-2d7304667b81488f947ae9b5969b5dba
Source dataset
uspto-grants-1987_04
Patent number
US04661635

Reaction notes

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