Mono-acylation of piperazine and homopiperazine via ionic immobilization

Tetrahedron Letters

Volumn 49, Issue 34, 2008, Pages 5047-5049

  Pringle, Wallace ^a  

^a NEUROGEN CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM DERIVATIVE; ION; METHANOL; PIPERAZINE; REAGENT; SILICA GEL; SULFONIC ACID DERIVATIVE;

ACYLATION; ARTICLE; CATALYSIS; IMMOBILIZATION; METHODOLOGY; SOLID; TITRIMETRY;

EID: 46749128089     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.06.044     Document Type: Article

References (14)

1. Lead in reference:. Prante O., Tietze R., Hocke C., Loeber S., Huebner H., Kuwert T., and Gmeiner P. J. Med. Chem. 51 (2008) 1800
2. Lead in reference:. Bettinetti L., Loeber S., Huebner H., and Gmeiner P. J. Comb. Chem. 7 (2005) 309
3. Lead in reference:. Troshina O.A., Troshin P.A., Peregudov A.S., Kozlovski V.I., and Lyubovskaya R.N. Chem.-Eur. J. 12 (2006) 5569
4. Carpino L.A., Mansour E.M.E., Cheng C.H., Williams J.R., MacDonald R., Knapczyk J., Carman M., and Lopusinski A. J. Org. Chem. 48 (1983) 661
5. For a non-traditional example see:. Das B., Venkateswarlu K., Krishnaiah M., and Holla H. Tetrahedron Lett. 47 (2006) 7551
6. Oliver M., Jorgensen M.R., and Miller A.D. Synlett (2004) 453
7. Poole C.F., and Poole S.K. In: Simpson N.J.K. (Ed). Solid-Phase Extraction: Principles, Techniques and Applications (2000), Marcel Dekker, New York 183-221
8. Organ M.G., Dixon C.E., Mayhew D., Parks D.J., and Arvanitis E.A. Comb. Chem. High Throughput Screen. 5 (2002) 211
9. SCX cartridges purchased from United Chemicals Technologies, Inc. Bristol, PA USA. Product name: 'CUBCX1 (Benzenesulfonic acid)'. Specifications: 500 mg in a 3 mL cartridge (loading = 0.7 meq/g). Loose SCX (i.e., not prepackaged in cartridge format) was purchased from the same supplier (and had the same loading).
10. Titration example: the amounts of 2a and 2b (both 450 μmol) and SCX (0.50 g) were held constant while increasing amounts of 1a were used. The yields of products (3a and 3c) obtained are plotted against the amount of 1a used.{A figure is presented}
11. In the reaction of 1a with 2a under the otherwise standard reaction conditions, the smaller the diameter of the reaction tube (i.e., the longer the SCX bed), the higher the yield of 3a.
12. With the small SCX cartridges (0.5-1.0 g SCX), the solvents were allowed to 'gravity drain'. Upon scale-up, the solvent was forced through the SCX bed with positive nitrogen pressure.
13. Suryakiran N., Prabhakar P., Reddy T.S., Rajesh K., and Venkateswarlu Y. Tetrahedron Lett. 47 (2006) 8039
14. Drying time under a 2 mmHg vacuum extended to 20 h.