Reacción #2195490

ord-88e5ef5a14e44e469a8964bd17a3b65b

Ecuación de reacción

O=C(Cl)c1cccs1
2-Thiophenecarbonylchloride
CC(C)(C)OC(=O)N1CCNCC1
tert-butyl-1-piperazinecarboxylate
CC(C)(C)OC(=O)N1CCN(C(=O)c2cccs2)CC1
solids
Rendimiento 88.1%
CC(C)(C)OC(=O)N1CCN(C(=O)c2cccs2)CC1
4-(Thiophene-2-carbonyl)-piperazine-1-carboxylic acid tert-butyl ester
Rendimiento 88.1%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Filtraciónthe precipitate was filtered
  2. 2
    Lavadowashed several times with water
  3. 3
    Otrodried

Procedimiento

2-Thiophenecarbonylchloride (2.04 g, 1.49 mL) was added to a solution of tert-butyl-1-piperazinecarboxylate (2.5 g, 13.4 mmol) and DMAP (20 mg) in pyridine (15 mL) at 0° C. under N2 atmosphere and stirred at room temperature for overnight. The mixture was poured into ice water, the precipitate was filtered, washed several times with water, and dried to yield white solids (3.5 g, 88%). Mp 76° C. 1H NMR (DMSO-d6): δ 1.42 (s, 12H), 3.40 (m, 4H), 3.61 (m, 4H), 7.12 (m, 1H), 7.43 (d, J=4.1 Hz, 1H), 7.77 (d, J=4.8 Hz, 1H). EIMS m/z 297 (M+1), 319 (M+23). Anal. (C14H20N2O3S) C, H, N.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07514225B2uspto-grants-2009_04