Synthesis and crystal structure of N-12-(7-chloro-4-quinolinyl)-N-1,N-1-diethyl-1,12-diaminododecane (AQ-40)

The preparation of N-12-(7-chloro-4-quinolinyl)-N-1,N-1-diethyl-1,12-diamin ododecane, AQ-40, was accomplished by a five-step process in 80% overall yi eld from 12-aminododecanoic acid and 4,7-dichloroquinoline. AQ-40 crystalli zes as a monohydrate from reagent grade chloroform/ diethyl ether mixtures in the triclinc space group P-1 with a = 8.667(2), b = 8.9425(10), c = 17.2 17(3) Angstrom, alpha = 99.34(1), beta = 99.89(2), gamma = 91.56(1)degrees V = 1295.0 Angstrom(3) and Z = 2. The 12-(N-1,N-1-diethylamino)dodecyl side chain is in the fully extended conformation and the water molecule forms h ydrogen bonds to the two tertiary nitrogen atoms as well as with the second ary amino group. The nitrogen of the secondary amino group bound to the fou r-position of the quinoline moiety is virtually planar. This together with the rather short C-N distance of 1.347(3) Angstrom to the quinoline moiety suggests involvement of the lone pair on this nitrogen with the pi system o f the ring.