Homopiperazine

Chemical properties

white to light yellow crystalline mass

The Uses of Homopiperazine

Homopiperazine is used to prepare 1,4-bis-(2-thiazolyl)-1,4-diazacycloheptane by reacting with 2-bromo-thiazole. It acts as an intermediate for repaglinide and fasudil hydrochloride. It is also used in the preparation of potent H3 receptor antagonists, which is used for the treatment of neurodegenerative conditions. Further, it is used in vesicant, cosmetic, emulsifier and energetic material. It acts as a corrosion inhibitor for iron. In pharmaceuticals, it is employed as antipyretic and reducing blood sugar, adiposity, calm, antipsychotic and anti-nervous.

The Uses of Homopiperazine

pharmaceutical intermediate

structure and hydrogen bonding

The conformation of Homopiperazine is shown below, and the N–C–C–N torsion angle of 58.2(4)° confirms that the left-hand end of the molecule has an almost ideal chair-type conformation, which is only slightly distorted by the insertion of the extra atom at the right-hand end. The two nitrogen lone pairs are aligned in opposite directions, which facilitates the formation of a hydrogen-bonded network due to interaction with the NH of adjacent molecules.    Crystal data for C5H12N2, M = 100.16 g mol^-1, colorless prism, crystal dimensions 0.10 × 0.10 × 0.10 mm³, tetragonal, space group I–42d (No. 122), a = b = 7.208(2), c = 23.094(7) Å, α = β = γ = 90.00°, V = 1199.9(6) ų, Z = 8, D_calc = 1.109 g cm^-3, T = 93 K, R1 = 0.0637, Rw2 = 0.1633 for 536 reflections with I > 2σ(I), and 37 variables, Rint 0.0374, goodness of fit on F² 1.137. Data have been deposited at the Cambridge Crystallographic Data Centre as CCDC 2049324[1].

References

[1] R. Aitken, A. Slawin, Dheirya K. Sonecha. “Homopiperazine (Hexahydro-1,4-diazepine).” Molbank 2021 1 (2021): M1200.