Propargyl bromide → 3-[4-(4-Prop-2-ynyloxy-phenyl)-piperazin-1-yl]-propionic acid methyl ester

HRID 12930Notes

Reaction equation

HRID 12930 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)C.C([O-])([O-])=O.[K+].[K+].Br[CH2:28][C:29]#[CH:30]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH2:5][N:7]1[CH2:8][CH2:9][N:10]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:30][C:29]#[CH:28])=[CH:17][CH:18]=2)[CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 684326753-[4-(4-Hydroxy-phenyl)-piperazin-1-yl]-butyric acid methyl ester

Product 1

HCID 866196573-[4-(4-Prop-2-ynyloxy-phenyl)-piperazin-1-yl]-propionic acid methyl esterYield 39.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of the compound from step 1 (278 mg, 1.0 mmol) and K2CO3 (152 mg, 1.1 mmol) in DMF (5 mL) was added 3-bromopropyne (130 mg, 1.1 mmol) dropwise at rt. The reaction mixture was stirred at rt overnight and then partitioned between water and ethyl acetate. The organic payers were combined and washed with brine, dried over anhydrous Na2SO4 and evaporated under vacuum to give a brown oil. The crude product was purified by silica gel flash chromatography (30% ethyl acetate in hexane) to furnish the title compound (120 mg, 38%) as a light yellow solid; MS; m/z 317 (M+H).

Workup

  1. custompartitioned between water and ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. customevaporated under vacuum
  5. customto give a brown oil
  6. customThe crude product was purified by silica gel flash chromatography (30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-8ca57d439fb34165987b64e0ae661fb3
Source dataset
uspto-grants-2010_06
Patent number
US07728032B2

Reaction notes

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