Reagents and conditions: (a)
for 15, 18, 23: 1-bromopropane;
for 16: ethyl bromoacetate; for 17, 21, 25: (4-bromobutoxy)benzene; for 20, 24: (3-bromopropoxy)benzene; for 19:
(2-bromoethoxy)benzene; for 22: methyl iodide; NaH, DMF,
r.t., 3 h; (b) H2, 10% Pd/C, THF/EtOH, r.t., 18 h; (c)
1 M NaOH; (d) methyl iodide, Cs2CO3, acetone,
60 °C, 48 h.