4-Chloropyridine hydrochloride → 4-(Pyridin-4-YL)piperazin-2-one

HRID 1290491Notes

Reaction equation

HRID 1290491 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][C:2]1=[O:7].Cl.Cl[C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1>>[N:13]1[CH:14]=[CH:15][C:10]([N:4]2[CH2:5][CH2:6][NH:1][C:2](=[O:7])[CH2:3]2)=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 818524-Chloropyridine hydrochlorideHCID 231360Piperazin-2-one

Product 1

HCID 189183564-(Pyridin-4-YL)piperazin-2-oneYield 23.5%

Conditions

Temperature
200 °C

Procedure

An intimate mixture of piperazinone (4.2 g) and 4-chloropyridine hydrochloride (7.33 g) was stirred and heated at 200° C. for 10 minutes and allowed to cool. The product was purified by flash column chromatography and cluted with 1/9/0.1 v:v:v methanol/methylene chloride/0.88 S.G. aqueous ammonia. The solid thus obtained was recrystallised from ethanol to give 4-(4-pyridyl)piperazin-2-one (1.75 g); m.p. 268°-270° C.; NMR (d6DMSO) δ 8.2(3H,m); 6.8(12H,m); 3.85(2H,s); 3.52(2H,m); 3.31(2H,m); m/e 178(M+H)+.

Workup

  1. temperatureto cool
  2. customThe product was purified by flash column chromatography
  3. customThe solid thus obtained
  4. customwas recrystallised from ethanol

Sources & evidence

ORD record
ord-e94f1e26e68d489da0de721b108a7220
Source dataset
uspto-grants-1998_05
Patent number
US05750754

Reaction notes

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