Abstract
The structure of 1,4-diphenylpiperazine (1) was determined; it crystallized in the orthorhombic space group Pbca, a = 8.6980(7), b = 8.4287(7), c = 17.6359(15), V = 1292.94(19), Z = 4. Three novel N,N′-disubstituted piperazines were synthesized via reductive amination of piperazine or N-diphenylmethylpiperazine. The products were characterized by NMR and X-ray crystallography. 1,4-Diphenethylpiperazine (2) crystallized in the monoclinic space group C2/c, a = 17.9064(13), b = 6.2517(5), c = 14.9869(11), β = 90.613(4), V = 1677.6(2), Z = 4. 1-Benzhydryl-4-benzylpiperazine (3) crystallized in the monoclinic space group Pn, a = 5.9450(2), b = 19.0722(4), c = 8.6084(2), β = 96.4600(10), V = 98.1790(10), Z = 2. 1-Benzhydryl-4-(pyridin-2-ylmethyl)piperazine (4) crystallized in the monoclinic space group P2/c, a = 13.5637(2), b = 5.82170(10), c = 24.0645(4), β = 90.613(4), V = 1888.16(5), Z = 4. Comparison of the structures showed significant sp2 character for the piperazine nitrogen atoms in 1. Each structure showed multiple intermolecular non-bonding interactions.
Graphical Abstract
The structures of 1,4-diphenylpiperazine, diphenethylpiperazine, 1-benzhydryl-4-benzylpiperazine, and 1-benzhydryl-4-(pyridin-2-ylmethyl)piperazine are reported.
Similar content being viewed by others
References
Choi Y-H, Baek DJ, Seo SH, Lee JK, Pae AN, Cho YS, Min S-J (2011) Bioorg Med Chem Lett 21:215–219
Rossi C, Porcelloni M, D’Andrea P, Fincham C, Ettorre A, Mauro S, Squarcia A, Bigioni M, Parlani M, Nardelli F, Binaschi M, Maggi CA, Fattori D (2011) Bioorg Med Chem Lett 21:2305–2308
Ratilainen J, Airola K, Fröhlich R, Nieger M, Rissanen K (1999) Polyhedron 18:2265–2273
Halfen JA, Uhan JM, Fox DC, Mehn MP, Que L Jr (2000) Inorg Chem 39:4913–4920
Ciccarese A, Clemente DA, Fanizzi FP, Marzotto A, Valle G (1998) Inorg Chim Acta 275:410–418
Ciccarese A, Clemente DA, Fanizzi FP, Marzotto A, Valle G (1998) Acta Crystallogr C 54:1779–1781
Beller M, Trauthwein H, Eichberger M, Breindl C, Muller TE, Zapf A (1998) J Organomet Chem 566:277–285
Anderson CE, Apperley DC, Battsanov AS, Dyer PW, Howard JAK (2006) Dalton Trans 4134–4145
Fritz T, Steinfeld G, Kersting B (2007) Z Naturforsch B 62:508–518
Hollo-Sitkei E, Tarkanyi G, Parkanyi L, Megyes T, Besenyi G (2008) Eur J Inorg Chem 1573–1583
Zhang W, Xiong RG, Huang S (2008) J Am Chem Soc 130:10468–10469
Obaidi NA, Harnor TA, Jones CJ, McCleverty JA, Paxton K (1987) J Chem Soc Dalton Trans 2653–2660
Soma T, Miyamoto TK, Iwamoto T (1997) Chem Lett 319
Stocker FB, Staeva TB, Rienstra CM, Britton D (1999) Inorg Chem 38:984–991
Yang S, Zou Y, Zhu H-L (2005) Acta Crystallogr E 61:m219–m220
Zhang R-F, Zhao B, Wang H-S, Cheng P (2007) Inorg Chem Commun 10:1226–1228
Yilmaz VT, Guney S, Kazak C (2008) Polyhedron 27:1381–1386
Farnum GA, Knapp WR, LaDuca RL (2009) Polyhedron 28:291–299
Braga D, Maini L, Mazzeo PP, Ventura B (2010) Chem Eur J 16:1553–1559
Lim MJ, Murray CA, Tronic TA, deKrafft KE, Ley AN, deButts JC, Pike RD, Lu H, Patterson HH (2008) Inorg Chem 47:6931–6947
Hou Q, Yu J-H, Xu J-N, Yang Q-F, Xu J-Q (2009) Inorg Chim Acta 362:2802–2806
Braga D, Grepioni F, Maini L, Mazzeo PP, Ventura B (2011) New J Chem 35:339–344
Ley AN, Dunaway LE, Brewster TP, Dembo MD, Harris TD, Baril-Robert F, Li X, Patterson HH, Pike RD (2010) Chem Commun 46:4565–4567
Dembo MD, Dunaway LE, Jones JS, Lepekhina EA, McCullough SM, Ming JL, Li X, Baril-Robert F, Patterson HH, Bayse CA, Pike RD (2010) Inorg Chim Acta 364:102–114
Miller KM, McCullough SM, Lepekhina EA, Thibau IJ, Pike RD, Li X, Killarney JP, Patterson HH (2011) Inorg Chem 50:7239–7249
Araki H, Tsuge K, Sasaki Y, Ishizaka S, Kitamura N (2005) Inorg Chem 44:9667–9675
Denmark SE, Fu J (2002) Org Lett 4:1951–1953
SAINT PLUS (2001) Bruker Analytical X-ray Systems, Madison, WI
SADABS (2001) Bruker Analytical X-ray Systems, Madison, WI
Sheldrick GM (2008) Acta Crystallogr A 64:112–122
Owston PG, Peters R, Ramsammy E, Tasker PA, Trotter J (1980) J Chem Soc Chem Commun 1218–1220
Gourdon A, Launay J-P, Bujoli-Doeuff M, Heisel F, Miehe J-A, Amouyal E, Boillet M-L (1993) J Photochem Photobiol A 71:13–25
Spange S, El-Sayed M, Muller H, Rheinwald G, Lang H, Poppitz W (2002) Eur J Org Chem 4159–4168
MacPhee JM, Guzman HL, Almarsson O (2003) J Am Chem Soc 125:8456–8457
Lynch DE, McClenaghan I (2004) Acta Crystallogr C 60:o1–o5
Cherkasov V, Druzhkov N, Kocherova T, Fukin G, Shavyrin A (2011) Tetrahedron 67:80–84
Naveen S, Swamy SN, Basappa B, Rangappa KS (2006) Anal Sci 22:x41–x42
Kumar CSA, Prasad SBB, Thimmegowda NR, Rangappa KS, Chandrappa S, Naveen S, Sridhar MA, Prasad JS (2007) Mol Cryst Liq Cryst 469:111–119
Vinaya K, Naveen S, Kumar CSA, Benakaprasad SB, Sridhar MA, Prasad JS, Rangappa KS (2008) Struct Chem 19:765–770
Amor FB, M’hamed MO, Mrabet H, Driss A, Efrit ML (2008) Acta Crystallogr E 64:o1872
Naveen S, Kumar CSA, Prasad SBB, Vinaya K, Prasad JS, Rangappa KS (2009) J Chem Crystallogr 39:395–398
Naveen S, Kumar CSA, Manjunath HR, Prasad SBB, Sridhar MA, Rangappa KS, Prasad JS (2009) Mol Cryst Liq Cryst 503:151–158
Zhang M, Zhou Y-H, Hou L-H, Yang X-H (2010) Acta Crystallogr E 66:o3336
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Safko, J.P., Pike, R.D. Synthesis and Crystal Structures of N,N′-Disubstituted Piperazines. J Chem Crystallogr 42, 981–987 (2012). https://doi.org/10.1007/s10870-012-0346-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10870-012-0346-1