(4-methylpyrrolidin-3-yl)methanamine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A mixture of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (0.5 g), β-picoline (11 ml) and 3-aminomethyl-4-methylpyrrolidine (0.5 g) was refluxed for 8.5 hours, then the reacting mixture was cooled to room temperature. To the mixture was added concentrated aqueous ammonia (100 ml) and concentrated under reduced pressure. To the residue was added dichloromethane-ether (1:3, 37 ml), the resulting precipitate was collected by filtration, washed with ethanol-ether (1:3), recrystallized from ethanol and further recrystallized from chloroform-methanol-concentrated aqueous ammonia (10:10:1) to give the title compound (0.14 g) as pale yellow powder, mp 245°-248° C. was refluxed for 8.5 hours concentrated under reduced pressure To the residue was added dichloromethane-ether (1:3, 37 ml) the resulting precipitate was collected by filtration washed with ethanol-ether (1:3) recrystallized from ethanol further recrystallized from chloroform-methanol-concentrated aqueous ammonia (10:10:1)

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

Procedure: A mixture of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (0.5 g), β-picoline (11 ml) and 3-aminomethyl-4-methylpyrrolidine (0.5 g) was refluxed for 8.5 hours, then the reacting mixture was cooled to room temperature. To the mixture was added concentrated aqueous ammonia (100 ml) and concentrated under reduced pressure. To the residue was added dichloromethane-ether (1:3, 37 ml), the resulting precipitate was collected by filtration, washed with ethanol-ether (1:3), recrystallized from ethanol and further recrystallized from chloroform-methanol-concentrated aqueous ammonia (10:10:1) to give the title compound (0.14 g) as pale yellow powder, mp 245°-248° C. was refluxed for 8.5 hours concentrated under reduced pressure To the residue was added dichloromethane-ether (1:3, 37 ml) the resulting precipitate was collected by filtration washed with ethanol-ether (1:3) recrystallized from ethanol further recrystallized from chloroform-methanol-concentrated aqueous ammonia (10:10:1)

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

Procedure: A mixture of 6,7,8-trifluoro-1-(2-fluoroethyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (0.5 g), anhydrous acetonitrile (5 ml), 3-aminomethyl-4-methylpyrrolidine (0.21 g) and DBU (0.26 g) was refluxed for an hour and then stirred at room temperature for 5 hours. The resulting precipitate was collected by filtration and washed with ether to give the title compound (0.45 g) as pale yellow powder, mp 228°-232° C. was refluxed for an hour The resulting precipitate was collected by filtration washed with ether

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

Procedure: A mixture of 1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (0.5 g), anhydrous acetonitrile (5 ml), 3-aminomethyl-4-methylpyrrolidine (0.22 g) and DBU (0.28 g) was refluxed for an hour and then stirred at room temperature for 3 hours. The resulting precipitate was collected by filtration and washed with ether to give the title compound (0.39 g) as pale yellow powder, mp 222°-224° C. was refluxed for an hour The resulting precipitate was collected by filtration washed with ether

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

Procedure: A mixture of 1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (0.5 g), anhydrous acetonitrile (5 ml), 3-aminomethyl-4-methylpyrrolidine (0.22 g) and DBU (0.28 g) was refluxed for an hour and then stirred at room temperature for 3 hours. The resulting precipitate was collected by filtration and washed with ether to give the title compound (0.39 g) as pale yellow powder, mp 222°-224° C. was refluxed for an hour The resulting precipitate was collected by filtration washed with ether

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

Procedure: A mixture of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (0.6 g), anhydrous acetonitrile (5 ml), 3-aminomethyl-4-methylpyrrolidine (0.29 g) and DBU (0.33 g) was refluxed for an hour and then stirred at room temperature for 2 hours and allowed to stand overnight. The resulting precipitate was collected by filtration and recrystallized from chloroform-methanol-concentrated aqueous ammonia (10:10:1) to give the title compound (0.45 g) as colorless prisms, mp 249°-252.5° C. was refluxed for an hour to stand overnight The resulting precipitate was collected by filtration recrystallized from chloroform-methanol-concentrated aqueous ammonia (10:10:1)

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

Procedure: A mixture of 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (0.6 g), anhydrous acetonitrile (5 ml), 3-aminomethyl-4-methylpyrrolidine (0.27 g) and 1,8-diazabicyclo[5,4,0]-7-undecene (DBU; 0.3 g) was refluxed for an hour and then stirred at room temperature for 7 hours. The resulting precipitate was collected by filtration and recrystallized from chloroform-methanol-concentrated aqueous ammonia (10:10:1) to give the title compound (0.26 g) as colorless prisms, mp 235°-238° C. was refluxed for an hour The resulting precipitate was collected by filtration recrystallized from chloroform-methanol-concentrated aqueous ammonia (10:10:1)

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

Procedure: A mixture of 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (0.6 g), anhydrous acetonitrile (5 ml), 3-aminomethyl-4-methylpyrrolidine (0.27 g) and 1,8-diazabicyclo[5,4,0]-7-undecene (DBU; 0.3 g) was refluxed for an hour and then stirred at room temperature for 7 hours. The resulting precipitate was collected by filtration and recrystallized from chloroform-methanol-concentrated aqueous ammonia (10:10:1) to give the title compound (0.26 g) as colorless prisms, mp 235°-238° C. was refluxed for an hour The resulting precipitate was collected by filtration recrystallized from chloroform-methanol-concentrated aqueous ammonia (10:10:1)

Conditions: temp:0.00; pressure:0.00; stir: