Reacción #44815

Ecuación de reacción

LiOH.H2O

benzoate

THF

→

benzoic acid

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was heated
2. 2
   Temperaturaat reflux
3. 3
   Temperaturato cool
4. 4
   Concentraciónconcentrated
5. 5
   workup.ADDITIONdiluted with water (3 mL)
6. 6
   FiltraciónThe solid was collected by filtration
7. 7
   Otrodried
8. 8
   Otrorecrystallized from water (5 mL)

Procedimiento

A solution of the methyl 4-[[4-(2,2,3,3,4,4,4-heptafluorobut-1-oxy)anilino]-1-piperidinyl]methyl]benzoate (0.59 g, 1.13 mmol) in a 3 to 1 mixture of THF and water (40 mL) was added LiOH.H2O (8 eq, 385 mg). The reaction mixture was heated at reflux with stirring for 10 h. The reaction was allowed to cool, concentrated, diluted with water (3 mL), and acidified to a pH of 6 with an aqueous solution of 2N HCl. The solid was collected by filtration, dried, and recrystallized from water (5 mL) to give 0.32 g of 4-[[4-(2,2,3,3,4,4,4-heptafluorobut-1-oxy)phenylamino]-1-piperidinyl]methyl]benzoic acid; 1H NMR (400 MHz, DMSO-d6) δ 7.86 (d, 2H), 7.38 (d, 2H), 6.668 (d, 2H), 6.50 (d, 2H), 4.60 (t, 2H), 3.50 (s, 2H), 3.30 (br., 1H), 3.10 (m, 1H), 2.75 (m, 2H), 2.05 (m, 2H), 1.85 (m, 2H), 1.30 (m, 2H) ppm.

Fuente