3,4-dihydro-2H-chromene-2-carbonitrile

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2.8 g 2-aminomethyl-chromane [obtainable by reacting 3-(2-hydroxy-phenyl)-propanal with KCN and subsequent catalytic reduction of the 2-cyano-chromane] and 2.2 g 3-chloromethyl)-pyridine in 250 ml of DMF are stirred together with 1 g N-methyl-morpholine for 12 hours at 20° and worked up in a conventional manner to give N-(3-pyridylmethyl)-N-(2-chromanyl-methyl)-amine. Stirring with 0.5 equivalents of maleic acid in 100 ml ethanol gives the maleate, m.p 163°-164°.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 23.7 g (0.338 mole) of methyl vinyl ketone were added over 5 minutes to a solution of 9.7 g (0.36 mole) of liquid hydrocyanic acid and 34 g of nitromethane whilst stirring, and thereafter 0.5 g of triethylamine was added slowly, first at -20° C. and then at -25° C. The reaction mixture was then kept at -20° C. for 1.5 hours. After acidifying the mixture with 1 g of phosphoric acid, 51.4 g (0.338 mole) of trimethylhydroquinone and 180 g of toluene were added, and 23.0 g (0.338 mole) of BF3 were then passed in over 1.5 hours at -10° C. After stirring for one hour at -5° C., the mixture was brought to room temperature and stirred for 5 hours. Working up by the method described in Example 1 gave pure 2-cyanochromane in 78% yield. at -25° C were added were then passed in over 1.5 hours at -10° C After stirring for one hour at -5° C. was brought to room temperature stirred for 5 hours

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 23.7 g (0.338 mole) of methyl vinyl ketone were added over 5 minutes to a solution of 9.7 g (0.36 mole) of liquid hydrocyanic acid and 34 g of nitromethane whilst stirring, and thereafter 0.5 g of triethylamine was added slowly, first at -20° C. and then at -25° C. The reaction mixture was then kept at -20° C. for 1.5 hours. After acidifying the mixture with 1 g of phosphoric acid, 51.4 g (0.338 mole) of trimethylhydroquinone and 180 g of toluene were added, and 23.0 g (0.338 mole) of BF3 were then passed in over 1.5 hours at -10° C. After stirring for one hour at -5° C., the mixture was brought to room temperature and stirred for 5 hours. Working up by the method described in Example 1 gave pure 2-cyanochromane in 78% yield. at -25° C were added were then passed in over 1.5 hours at -10° C After stirring for one hour at -5° C. was brought to room temperature stirred for 5 hours

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2.8 g 2-aminomethyl-chromane [obtainable by reacting 3-(2-hydroxy-phenyl)-propanal with KCN and subsequent catalytic reduction of the 2-cyano-chromane] and 2.2 g 3-chloromethyl)-pyridine in 250 ml of DMF are stirred together with 1 g N-methyl-morpholine for 12 hours at 20° and worked up in a conventional manner to give N-(3-pyridylmethyl)-N-(2-chromanyl-methyl)-amine. Stirring with 0.5 equivalents of maleic acid in 100 ml ethanol gives the maleate, m.p 163°-164°.