Reaction #2338

Reaction equation

methyl 4-[2-(piperazin-2-one-1-yl)acetyl]-phenoxyacetate

4-chloropyridine hydrochloride

triethylamine

→

title compound

Yield 40.7%

4-[2-[4-(4-pyridyl)piperazin-2-one-1-yl]acetyl]-phenoxyacetic acid monohydrochloride

Yield 40.7%

Solvents

water

dioxan

Conditions

Workup

1. 1
   Otherevaporated to dryness
2. 2
   OtherThe residue was triturated with water (2 ml)
3. 3
   Filtrationfiltered
4. 4
   OtherThe solid thus obtained
5. 5
   Otherwas recrystallised from water

Procedure

A solution of methyl 4-[2-(piperazin-2-one-1-yl)acetyl]-phenoxyacetate (0.347 g), 4-chloropyridine hydrochloride (0.19 g) and triethylamine (0.178 g) in water (8 ml) and dioxan (1 ml) was heated on a steam bath for 2 hours and then evaporated to dryness. The residue was triturated with water (2 ml) and filtered. The solid thus obtained was recrystallised from water to give the title compound (0.187 g), m.p. 275°-277° C.; NMR(d6DMSO δ 8.33(2H,d), 8.0(2H,d), 7.21(2H,d), 7.1(2H,d), 4.97(2H,s), 4.81(2H,s), 3.94(2H,m), 3.59(2H,m); m/e 370(H+H)+ ; calculated for C19H20N3O5Cl. 0.75 H2O: C, 54.4; H, 5.0; N, 10.0. Found: C, 54.5; H, 5.3; N, 9.5%.

Source