Reaction #2316

Reaction equation

product

Methyl 4-[2-[4-(4-pyridyl)piperazin-1-yl]acetyl]-phenoxyacetate

ammonia

→

title compound

4-[2-[4-(4-Pyridyl)piperazin-1-yl]acetyl]phenoxy-acetamide

Solvents

methanol

Conditions

Workup

1. 1
   Othersealed in a pressure bottle
2. 2
   OtherThe orange crystals which formed
3. 3
   Filtrationafter filtration
4. 4
   Washwashing with a little methanol

Procedure

A solution of the product of Example 1 (200 mg) in methanol (10 ml), prepared under argon, was cooled to 4° C. and saturated with dry ammonia gas, then sealed in a pressure bottle and kept for 2 days. The orange crystals which formed, after filtration and washing with a little methanol, gave the title compound, 140 mg: m.p. 247° to 248° C.; NMR (d6DMSO) δ 8.16 (2H, d), 7.99 (2H, d), 7.55 (1H, bs), 7.37 (1H, bs), 7.02 (2H, d), 6.81 (2H, d), 4.54 (2H, s), 3.85 (2H, s), 3.33 (4H, t), 2.60 (4H, t); m/e 355 (M+H)+ ; calculated for C19 H22N4O3 : C, 64.4; H, 6.3; N, 15.8. found: C, 64.4; H, 6.4; N, 15.6%.

Source