Diisopropylethylamine → 4-(2-(Pyridin-2-yl)ethyl)piperazin-2-one

HRID 474953Notes

Reaction equation

HRID 474953 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][C:2]1=[O:7].Cl.Cl[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.CCN(C(C)C)C(C)C>>[N:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][CH2:10][N:4]1[CH2:5][CH2:6][NH:1][C:2](=[O:7])[CH2:3]1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 199467Pyridine, 2-(2-chloroethyl)-, hydrochlorideHCID 231360Piperazin-2-one

Product 1

HCID 580934314-(2-(Pyridin-2-yl)ethyl)piperazin-2-oneYield 33.2%

Procedure

Piperazinone (2.2 g, 22 mmol), 2-(2-chloroethyl)pyridine hydrochloride (3.9 g, 22 mmol) and i-Pr2NEt (5.67 g, 7.6 mL, 44 mmol) were heated at reflux for 16 h. The mixture was concentrated, and the residue was purified by column chromatography (80 g ISCO column eluting with methylene chloride and a 10:1 methanol/ammonium hydroxide mixture; gradient 100% methylene chloride to 90% methylene chloride) to provide the title compound (1.5 g, 33%) as a yellow solid; ESI MS m/z 206 [M+H]+.

Workup

  1. temperatureat reflux for 16 h
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified by column chromatography (80 g ISCO column
  4. washeluting with methylene chloride

Sources & evidence

ORD record
ord-cf4f10a2c03f439caa2b6f9546401973
Source dataset
uspto-grants-2014_01
Patent number
US08637501B2

Reaction notes

Loading…