Reacción #506576

Ecuación de reacción

1,1-dimethylethyl 4-{4-[3-(methyloxy)-4-nitrophenyl]-1-piperazinyl}-1-piperidinecarboxylate

TFA

→

title compound

Rendimiento 93.0%

1-[3-(methyloxy)-4-nitrophenyl]-4-(4-piperidinyl)piperazine

Rendimiento 93.0%

Disolventes

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroUpon completion, by TLC, the reaction mixture was quenched with 1N NaOH (300 mL)
2. 2
   Extracciónextracted with DCM
3. 3
   Secadodried (MgSO4)
4. 4
   Concentraciónconcentrated

Procedimiento

A solution of 1,1-dimethylethyl 4-{4-[3-(methyloxy)-4-nitrophenyl]-1-piperazinyl}-1-piperidinecarboxylate (5.67 g, 13.5 mmol) and DCM (110 mL) was cooled with an ice/H2O bath. TFA (30.0 mL, 389 mmol) was added dropwise via addition funnel. Upon completion, by TLC, the reaction mixture was quenched with 1N NaOH (300 mL), extracted with DCM, dried (MgSO4) and concentrated to provide the title compound of step D (4.01 g, 12.5 mmol, 93%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.20-1.31 (m, 2H), 1.68 (d, J=9.9 Hz, 2H), 2.22-2.32 (m, 2H), 2.34-2.45 (m, 2H), 2.54-2.61 (m, 4H), 2.95 (d, J=12.1 Hz, 2H), 3.36-3.43 (m, 4H), 3.88 (s, 3H), 6.50 (d, J=2.6 Hz, 1H), 6.57 (dd, J=9.4, 2.4 Hz, 1H), 7.86 (d, J=9.5 Hz, 1H).

Fuente