Triethylamine → 3-[4-(4-Hydroxy-phenyl)-piperazin-1-yl]-butyric acid methyl ester

HRID 12929

Reaction equation

HRID 12929 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[CH:15]([CH3:21])[CH2:16][C:17]([O:19][CH3:20])=[O:18].C(N(CC)CC)C>CN(C=O)C>[CH3:20][O:19][C:17](=[O:18])[CH2:16][CH:15]([N:4]1[CH2:3][CH2:2][N:1]([C:7]2[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=2)[CH2:6][CH2:5]1)[CH3:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 89470Butanoic acid, 3-bromo-, methyl esterHCID 92467p-(1-Piperazinyl)phenol

Product 1

HCID 684326753-[4-(4-Hydroxy-phenyl)-piperazin-1-yl]-butyric acid methyl esterYield 59.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-piperazin-1-yl-phenol (2 g, 11.2 mmol) and methyl 3-bromo-butyrate (2.03 g, 11.2 mmol) in DMF (5 mL) was added triethylamine (4.5 mL, 11.53 mmol) dropwise and the reaction mixture was stirred at ambient temperature overnight. The mixture was poured onto water and extracted with ethyl acetate (50 ml×3). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and evaporated under vacuum to dryness. The residue was purified by silica gel flash chromatography (1% methanol in CH2Cl2) to furnish the title compound (1.85 g, 59.3%); MS; m/z 279 (M+H).

Workup

  1. additionThe mixture was poured onto water
  2. extractionextracted with ethyl acetate (50 ml×3)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customevaporated under vacuum to dryness
  6. customThe residue was purified by silica gel flash chromatography (1% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-8b0039b8c75446b48104676c801868df
Source dataset
uspto-grants-2010_06
Patent number
US07728032B2

Linked notes

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