As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO257,mainly used in chemical industry, its synthesis route is as follows.,1121-22-8
19.36 g of anhydrous magnesium sulphate (161.1 mmoles) and 6.44 ml of rac-trans-1,2-diaminocyclohexane (53.6 mmoles) were successively added to a solution of 10 ml of 2-thienylaldehyde (107.1 mmoles) in 75 ml of absolute ethanol. The reaction mixture was stirred for 16 hours at ambient temperature (the solution thickened very rapidly), heated for 2 hours under reflux then filtered through a frit. The isolated solid was washed with dichloromethane. The total filtrate was concentrated completely under reduced pressure to isolate a brown solid which was re-crystallised from ethanol. 14.0 g of beige crystals were obtained, corresponding to a yield of 86%. The characteristics were as follows: M.Pt: 173-175 C. (EtOH); 1H NMR/CDCl3: delta 8.27 (s, 2H, H7,14), 7.27 (m, 2H, H1,2), 7.14 (m, 2H, H5,16), 6.96 (m, 2H, H3,4), 3.32 (m, 2H, H8,13), 1.82 (m, 6H, H10,11 and H carried by carbons 9 and 12 located in the position cis (or trans) with respect to the adjacent nitrogen atoms), 1.44 (m, 2H, H carried by carbons 9 and 12 located in the trans (or cis) position with respect to the adjacent nitrogen atoms). 13C NMR/CDCl3: delta 154.32 (C7 and C14), 142.54 (C6 to C15), 130.09 (C1 and C2), 128.20 (C5 and C16), 127.18 (C3 and C4), 73.38 (C8 and C13), 32.83 (C9 and C12), 24.44 (C10 and C11).
With the synthetic route has been constantly updated, we look forward to future research findings about trans-Cyclohexane-1,2-diamine,belong chiral-catalyst compound
Reference£º
Patent; Taillefer, Marc; Cristau, Henri-Jean; Cellier, Pascal-Philippe; US2005/234239; (2005); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare