Phenylacetylene → HCID 14025506, compound

HRID 1199083Notes

Reaction equation

HRID 1199083 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][CH2:11][N:12]([CH3:14])[CH3:13].[C:15]1([C:21]#[CH:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=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>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:22]#[C:21][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:3]([CH2:10][CH2:11][N:12]([CH3:14])[CH3:13])[CH:4]=1

Participants

6

Reactant 2

HCID 10821PhenylacetyleneHCID 140255002-iodo-5-methoxy-N,N-dimethylbenzeneethanamine

Product 1

HCID 14025506HCID 14025506, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolvent

Procedure

To a solution of 1 g (3.3 mmoles) of 2-iodo-5-methoxy-N,N-dimethylbenzeneethanamine and 0.33 g (3.3 mmoles) phenylacetylene in 18 ml dry triethylamine were added, under nitrogen, 23.1 mg bis(triphenylphosphine) palladium (II) chloride and 11.4 mg Copper (I) iodide. The reaction mixture was stirred overnight. The yield by glc using internal standard of 5-methoxy-N,N-dimethyl-2-(phenylethynyl)benzeneethanamine was 91%.

Sources & evidence

ORD record
ord-45a6917bcef2448cb39abc5e3023efd5
Source dataset
uspto-grants-1990_02
Patent number
US04898889

Reaction notes

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