Chloroform → HCID 86586014, compound

HRID 432944Notes

Reaction equation

HRID 432944 reaction equation
C(OCCN1CC[N:12]([C:15](=[O:19])[CH2:16][CH2:17][CH3:18])CC1)(=O)CCC.[OH:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27]N[CH2:25][CH2:24]1.C(Cl)(Cl)[Cl:30]>>[ClH:30].[N:23]1([CH2:24][CH2:25][CH:16]([CH2:17][CH3:18])[C:15]([NH2:12])=[O:19])[CH2:22][CH2:21][O:20][CH2:27][CH2:28]1

Participants

4

Reactant 3

HCID 6212Chloroform2×HCID 76771-(2-Hydroxyethyl)piperazineHCID 9881903HCID 9881903, compound

Product 1

HCID 86586014HCID 86586014, compoundYield 94%

Procedure

Synthesis of 2-(4-Butanoylpiperazinyl)ethyl butanoate (BEB) 3 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 CI 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-a70e221cd3da484c8d2efa385bbad4da
Source dataset
uspto-grants-2003_12
Patent number
US06664394B2

Reaction notes

Loading…