Bromide ion → 1-[4-(4-Methyl-piperazin-1-yl)-phenyl]-prop-2-yn-1-ol

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[Br-].[Cl-].[NH4+].[CH2:19]1COC[CH2:20]1>>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:15]=[CH:14][C:11]([CH:12]([OH:13])[C:19]#[CH:20])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

Reactant 4

HCID 259Bromide ion

HCID 8028Tetrahydrofuran

HCID 25517Ammonium Chloride

HCID 7365334-(4-Methylpiperazin-1-yl)benzaldehyde

Product 1

HCID 577141411-[4-(4-Methyl-piperazin-1-yl)-phenyl]-prop-2-yn-1-olYield 84.2%

Procedure

To a solution of 4-(4-methyl-piperazin-1-yl)-benzaldehyde (28.9 mmol) in THF (100 ml), ethnylmagnesium bromide (0.5M solution in THF) (43.4 mmol) is added at 78° C. The solution is then stirred at room temperature for 18 h. The reaction mixture is treated with saturated ammonium chloride and extracted with ethyl acetate. The organic layer is washed with brine, dried over magnesium sulfate and evaporated down. CH2Cl2 is added to the residue to afford a precipitate, which is collected by filtration. yield 84.2%, Rf=0.23 (CH2Cl2:MeOH=9:1).