Reaction #2337

Reaction equation

product

4-[4-[4-(4-pyridyl)piperazin-1-yl]phenoxy]butyric acid

methanol

pyridine hydrochloride

→

title compound

Yield 81.3%

4-[4-[4-(4-pyridyl)piperazin-1-yl]phenoxy]butyric acid, hydrochloride salt

Yield 81.3%

Solvents

ethyl acetate

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureto reflux
3. 3
   TemperatureHeating
4. 4
   OtherThe reaction mixture was evaporated until a slight turbidity
5. 5
   OtherOn further cooling, a precipitate formed which
6. 6
   Otherwas collected
7. 7
   Washwashed with ethyl acetate
8. 8
   Otherdried

Procedure

A mixture of the product from Example 26 (1.5 g) and methanol (80 ml) was heated to reflux with stirring, and solid pyridine hydrochloride (0.5 g) was added. Heating was stopped and ethyl acetate (10 ml) was added. The reaction mixture was evaporated until a slight turbidity was observed. On further cooling, a precipitate formed which was collected, washed with ethyl acetate and dried to give the title compound (1.33 g) as a beige solid: m.p.>240° C. (dec); NMR (d6 -DMSO) δ 1.90 (2H, m), 2.36 (2H, t), 3.17 (4H, m), 3.83 (4H, m), 3.91 (2H, t), 6.89 (4H, q), 7.26 (2H, d), 8.25 (2H, d), 12.1 (1H, br), 13.75 (1H, br); m/Z 342 (M+H)+ ; calculated for C19H23N3O3. 1.0 HCl: C, 60.4%; H, 6.4%; N, 11.1%; found: C, 60.0%; H, 6.4%, N, 10.8%.

Source