synthesis of N-BOC-1,6-diaminohexane: 1,6-Diaminohexane 3 (Fig. 1) (100 g, 0.86 mol) was dissolved in CH2Cl2 (300 ml) and cooled in an ice bath to 0–3°C. To the stirred solution 0.3 eq. di-tert-butyl bicarbonate (62.6 g, 0.29 mol) was added slowly over a period of 1 h. The reaction was allowed to warm up to r.t., and proceeded overnight. The reaction mixture was extracted with saturated aqueous NaHCO3 (50 ml, three times). The organic phases were pooled, dried, and evaporated under reduced pressure. The resulting oil was dissolved in 200 ml, 1 N HCl and extracted with ether. The aqueous phase was washed with ether, made basic to a pH of 10 with aqueous 2 N NaO3, and extracted with ethyl acetate. The organic phases were pooled, dried, and evaporated under reduced pressure. The resulting oil was dissolved in 200 ml, 1 N HCL and extracted with ether. The aqueous phase was washed with ether, made basic to a pH of 10 with aqueous 2 N NaOH, and extracted with ethyl acetate. The organic extracts were pooled, dried over Na2SO4 and evaporated to give 10.5 g of homogeneous N-BOC-1, 6- diaminohexane 2c (Fig. 1) as a yellow oil which was used without further purification.
TLC Rf 0.51; 1H NMR (CDCL3) d 4.54 (bs, 1H; NH), 3.05 1 2.62 (m, 4H; NCH2), 1.41 (m, 9H; CH3), 1.29 (m, 8H; CH2).
Evaluation of aminoalkylmethacrylate nanoparticles as colloidal drug carrier systems. Part I: synthesis of monomers, dependence of the physical properties on the polymerization methods
