1: 93 percent / Na2CO3, propylene glycol / 3.5 h / 130 °C 2: 88 percent / odorless mineral spirits / 16 h / 140 °C 3: 1.) tetrabutylammonium hydrogen sulfate, 50percent NaOH, 3.) H2 / 3.) 5percent Pd/C / 1.) toluene, 35 deg C, 1 h; 20 deg C, 16 h, 2.) toluene, 20 deg C, 1 h, 3.) EtOH, 60 deg C, 55 psi, 16 h View Scheme

1: 88 percent / odorless mineral spirits / 16 h / 140 °C 2: 1.) tetrabutylammonium hydrogen sulfate, 50percent NaOH, 3.) H2 / 3.) 5percent Pd/C / 1.) toluene, 35 deg C, 1 h; 20 deg C, 16 h, 2.) toluene, 20 deg C, 1 h, 3.) EtOH, 60 deg C, 55 psi, 16 h View Scheme

sodium hydroxide; hydrogen; tetra(n-butyl)ammonium hydrogensulfate; palladium on activated charcoal 1.) toluene, 35 deg C, 1 h; 20 deg C, 16 h, 2.) toluene, 20 deg C, 1 h, 3.) EtOH, 60 deg C, 55 psi, 16 h; Yield given. Multistep reaction;

4-methyl-morpholine; hydrogenchloride T=80°C; 9 h;