Triethylamine → Methyl 4-(4-(2-tert-butylphenyl)-piperazin-1-yl)-4-oxobutanoate

HRID 534913Notes

Reaction equation

HRID 534913 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl[C:25](=[O:32])[CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29]>C(Cl)Cl>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:25](=[O:32])[CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH2:13][CH2:12]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 469416591-(2-Tert-butylphenyl)piperazine

Product 1

HCID 66750827Methyl 4-(4-(2-tert-butylphenyl)-piperazin-1-yl)-4-oxobutanoateYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution at 0° C. of 1-(2-tert-butylphenyl)piperazine (0.218 g, 1.00 mmol) and triethylamine (0.303 g, 3.00 mmol) in methylene chloride (5.0 mL) was added methyl 4-chloro-4-oxobutanoate (0.171 g, 1.10 mmol) and the resulting reaction mixture was warmed to room temperature. After 2 h the reaction mixture was diluted with methylene chloride (10.0 mL), washed with water (20.0 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, 50% ethyl acetate/heptanes) to provide methyl 4-(4-(2-tert-butylphenyl)-piperazin-1-yl)-4-oxobutanoate (0.245 g, 74%) as an off-white solid.

Workup

  1. customthe resulting reaction mixture
  2. washwashed with water (20.0 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash column chromatography (silica gel, 50% ethyl acetate/heptanes)

Sources & evidence

ORD record
ord-ad80c29007a44cfa9dbc767329aab329
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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