Triethylamine → HCID 67663315, compound

HRID 352194Notes

Reaction equation

HRID 352194 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)Br.CCN(CC)CC.[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1>O1CCCC1>[CH3:1][O:2][C:3](=[O:12])[CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[N:29]1[CH2:30][CH2:31][N:26]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][N:20]=2)[CH2:27][CH2:28]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 944591-(2-Pyridyl)piperazineHCID 137806Benzeneacetic acid, alpha-bromo-, methyl ester

Product 1

HCID 67663315HCID 67663315, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of racemic α-bromophenylacetic acid methyl ester, 5.0 g (22.0 mmol) in 200 mL of tetrahydrofuran was added 3.4 mL (22.0 mmol) of Et3N and 10 mL (66.0 mmol) of 1-(2-pyridyl)-piperazine. The reaction mixture was refluxed for five hours, cooled to rt. and concentrated to dryness. The residue was partitioned between 20% isopropanol/chloroform and water. The mixture was washed with saturated NaHCO3, washed with brine, dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by column chromatography using MeOH/chloroform as eluant and concentrated to dryness to give a quantitative yield of the desired mixture of isomers as a yellow oil. MS (ion spray) 312.2 (M+).

Workup

  1. temperatureThe reaction mixture was refluxed for five hours
  2. concentrationand concentrated to dryness
  3. customThe residue was partitioned between 20% isopropanol/chloroform and water
  4. washThe mixture was washed with saturated NaHCO3
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe residue was purified by column chromatography
  10. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-6a8986e4be8745f9be180d538a3a3c5c
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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