1-(2-Hydroxyethyl)piperazine → HCID 9881903, compound

HRID 1796905Notes

Reaction equation

HRID 1796905 reaction equation
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].[OH:7][CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1>C(Cl)(Cl)Cl>[C:1]([O:7][CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][N:13]([C:1](=[O:5])[CH2:2][CH2:3][CH3:4])[CH2:12][CH2:11]1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 76771-(2-Hydroxyethyl)piperazineHCID 8855Butyryl chloride

Product 1

HCID 9881903HCID 9881903, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Butyryl chloride (11.83 g, 0.11 mol) was added dropwise to a cooled solution of 4.84 g (0.04 mol) of 1-(2-hydroxyethyl)-piperazine in 20 ml of chloroform. Cooling was maintained for 2 h, and a white precipitate formed. Chloroform (15 ml) was added and the mixture was stirred overnight, washed with 210 ml of cold 0.6 N sodium hydroxide solution, then washed twice with 50 ml of cold water. The organic fraction was dried over anhydrous sodium sulfate, filtered and, concentrated in vacuo to yield 9.39 g (94%) of a clear yellow liquid. This was distilled: bp 144–146° C., (0.5 mm Hg) to give 6.08 g (65%) of MEB. 1H NMR (CDCl3) δ 0.897 (t, 3H, J=7.4, CH3), 0.901 (t, 3H, J=7.4, CH3), 1.59 (m, 2H, CH3CH2), 1.61 (m, 2H, CH3CH2), 2.24 (t, 2H, J=7.4 CH2CO), 2.25 (t, 2H, J=7.4, CH2CO), 2.42–2.43 (app t, 2H, J=5.2, axial CH ester end of ring), 2.43–2.44 (app t, 2H, J=5.2, equatorial CH ester end of ring), 2.59 (t, 2H, J=5.8, N—CH2—CH2—O), 3.41 (app t, 2H, axial CH amide end of ring), 3.57 (app t, 2H, equatorial CH amide end of ring), 4.16 ( t, 2H, N—CH2—CH2—O); MS m/z 270 (M+), 255, 242, 227, 199, 182, 169 (Base Peak).

Workup

  1. temperatureCooling
  2. temperaturewas maintained for 2 h
  3. customa white precipitate formed
  4. washwashed with 210 ml of cold 0.6 N sodium hydroxide solution
  5. washwashed twice with 50 ml of cold water
  6. dry with materialThe organic fraction was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-532fc7dd542749a2b507b9e6aa3c57a0
Source dataset
uspto-grants-2006_04
Patent number
US07034020B2

Reaction notes

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