1: (Z)-N-(3-chloro-2-propenyl)-N-methyl-1-naphthalenemethanamine; (E)-N-methyl N-naphthyl methylene-3-chloro-prop-2-en-1-amine With piperidine; copper(l) iodide; 10 platinum on carbon T=20 - 80°C; 0.5 h; 2: 3,3-dimethylbut-1-yne T=40°C; 4 h; 3: in water; toluene 0.25 h;

1: (E)-N-(3-chloro-2-propenyl)-N-methyl-1-naphthalenemethanamine oxalate; (Z)-N-(3-chloro-2-propenyl)-N-methyl-1-naphthalenemethanamine oxalate With piperidine; copper(l) iodide; 10 platinum on carbon T=20 - 80°C; 0.5 h; 2: 3,3-dimethylbut-1-yne T=40°C; 4 h; 3: in water; toluene 0.25 h;

sodium hydroxide in tetrahydrofuran; water; acetonitrile pH=6.5; Aqueous phosphate buffer;

potassium carbonate in water T=60°C; 9 h;

1: 1.) n-BuLi / 1.) THF, hexane, -15 to -20 deg C, 2.) THF, hexane, RT, overnight 2: 1.) aq. HBr, PBr3, 2.) Na2CO3 / 1.) EtOH, 2.) DMF, RT, overnight View Scheme

hydrogen bromide; phosphorus tribromide; sodium carbonate 1.) EtOH, 2.) DMF, RT, overnight; Yield given. Multistep reaction. Yields of byproduct given;