1-(2-Hydroxyethyl)piperazine → Methyl 4-(2-hydroxyethyl)-α-phenyl-1-piperazineacetate

HRID 352193Notes

Reaction equation

HRID 352193 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.[OH:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>O1CCCC1>[CH3:1][O:2][C:3](=[O:12])[CH:4]([N:26]1[CH2:27][CH2:28][N:23]([CH2:22][CH2:21][OH:20])[CH2:24][CH2:25]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 76771-(2-Hydroxyethyl)piperazineHCID 8471TriethylamineHCID 137806Benzeneacetic acid, alpha-bromo-, methyl ester

Product 1

HCID 69848748Methyl 4-(2-hydroxyethyl)-α-phenyl-1-piperazineacetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of racemic a-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 8 mL (66.0 mmol) of 1-(hydroxyethyl)piperazine. The reaction mixture was refluxed for three 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 to give a quantitative yield of the desired mixture of isomers as a yellow oil. MS (ion spray) 279.1 (M+).

Workup

  1. temperatureThe reaction mixture was refluxed for three 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

Sources & evidence

ORD record
ord-8947aa8ce25c4fb79c9d23900156d215
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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