Method A. The appropriate secondary amine was alkylated using w-chloroalkylnitriles, usually 5-chlorovaleronitrile. The nitriles thus formed (compounds 14-26, 29, 33, 34, 36, 37, and 40, Table I) were then reduced to the corresponding primary amine using LiAlH4. This yielded the inhibitors 47, 48, 52-56, 61, 62, 64, 71, 73-75 and 77-80.
[Arimori, Susumu; Bell, Michael L.; Oh, Chan S.; Frimat, Karine A.; James, Tony D. Journal of the Chemical Society. Perkin Transactions 1, 2002 , # 6 p. 803 - 808]