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

HRID 1984234Notes

Reaction equation

HRID 1984234 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

5

Reactant 4

HCID 259Bromide ionHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 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).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated down
  5. additionCH2Cl2 is added to the residue
  6. customto afford a precipitate, which
  7. filtrationis collected by filtration

Sources & evidence

ORD record
ord-d33b165786d645b583b26029133da356
Source dataset
uspto-grants-2009_06
Patent number
US07544688B2

Reaction notes

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