2-(4-methylpiperidin-1-yl)ethanamine

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

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

Procedure: A solution of 12.02 g (32.45 mmol) of 2-(4-methylpiperidin-1-yl)ethylamine in 100 mL of DMF is combined with 17.94 g (64.82 mmol) of potassium carbonate and stirred for 15 minutes at ambient temperature. Then 5.81 g (32.45 mmol) of 3-chloro-4-fluoronitrobenzene are added and the reaction mixture is stirred for 18 hours. Then the reaction mixture is poured into ice water and the crystalline residue is filtered off. Yield: 8.85 g (91.6% of theory); C14H20ClN3O2 (M=297.78); calc.: molecular ion peak (M+H)+: 298/300; found: molecular ion peak (M+H)+: 298/300. the reaction mixture is stirred for 18 hours the crystalline residue is filtered off

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

Procedure: The product was obtained analogously to Example 20.1a starting from 5-(4-chlorophenyl)-2-(4-iodothiophen-2-ylethynyl)pyridine and 2-(4-methylpiperidin-1-yl)ethylamine. Yield: 3 mg (1% of theoretical); C25H26ClN3S (M=436.013); calc.: molpeak (M+H)+: 436/438 (Cl); found: molpeak (M+H)+: 436/438 (Cl); HPLC-MS: 5.10 minutes (method B). The product was obtained analogously to Example 20.1a 5.10 minutes (method B)

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

Procedure: 5.00 g (35.00 mmol) of 2-(4-methylpiperidin-1-yl)ethylamine was added under argon to a mixture of 10.39 g (35.00 mmol) of 4-bromo-1-iodo-2-methylbenzene, 0.33 g (1.75 mmol) of CuI, 30.0 g (141.00 mmol) of potassium phosphate, and 4.34 g (70.00 mmol) of ethylene glycol in 35 mL of isopropanol and the mixture was refluxed for 15 hours. The reaction mixture was evaporated down in vacuo and the residue taken up in EtOAc. The organic phase was washed with 5% aqueous ammonia, dried over magnesium sulfate, and evaporated down in vacuo. The crude product was purified by column chromatography (silica gel, EtOAc). Yield: 1.20 g (11% of theoretical); C15H23BrN2 (M=311.261); calc.: molpeak (M+H)+: 311/313 (Br); found: molpeak (M+H)+: 311/313 (Br); HPLC-MS: 4.24 minutes (method B). the mixture was refluxed for 15 hours The reaction mixture was evaporated down in vacuo The organic phase was washed with 5% aqueous ammonia dried over magnesium sulfate evaporated down in vacuo The crude product was purified by column chromatography (silica gel, EtOAc) 4.24 minutes (method B)

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

Procedure: 5.00 g (35.00 mmol) of 2-(4-methylpiperidin-1-yl)ethylamine was added under argon to a mixture of 10.39 g (35.00 mmol) of 4-bromo-1-iodo-2-methylbenzene, 0.33 g (1.75 mmol) of CuI, 30.0 g (141.00 mmol) of potassium phosphate, and 4.34 g (70.00 mmol) of ethylene glycol in 35 mL of isopropanol and the mixture was refluxed for 15 hours. The reaction mixture was evaporated down in vacuo and the residue taken up in EtOAc. The organic phase was washed with 5% aqueous ammonia, dried over magnesium sulfate, and evaporated down in vacuo. The crude product was purified by column chromatography (silica gel, EtOAc). Yield: 1.20 g (11% of theoretical); C15H23BrN2 (M=311.261); calc.: molpeak (M+H)+: 311/313 (Br); found: molpeak (M+H)+: 311/313 (Br); HPLC-MS: 4.24 minutes (method B). the mixture was refluxed for 15 hours The reaction mixture was evaporated down in vacuo The organic phase was washed with 5% aqueous ammonia dried over magnesium sulfate evaporated down in vacuo The crude product was purified by column chromatography (silica gel, EtOAc) 4.24 minutes (method B)

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

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

Procedure: A solution of 5.0 g of 6-chloro-7,8,9,10-tetrahydro-1,2,4-triazolo[3,4-a]phthalazine in 25 ml of 1-(2-aminoethyl)-4-methylpiperidine was heated at reflux for 15 hours and then poured into ice water. The resulting off-white solid was separated by filtration and recrystallized from toluene to give 6-[2-(4-methyl-1-piperidinyl)ethylamino]-7,8,9,10-tetrahydro-1,2,4-triazolo[3,4-a]phthalazine melting at about 180°-181° C. at reflux for 15 hours The resulting off-white solid was separated by filtration recrystallized from toluene

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

Procedure: A solution of 12.02 g (32.45 mmol) of 2-(4-methylpiperidin-1-yl)ethylamine in 100 mL of DMF is combined with 17.94 g (64.82 mmol) of potassium carbonate and stirred for 15 minutes at ambient temperature. Then 5.81 g (32.45 mmol) of 3-chloro-4-fluoronitrobenzene are added and the reaction mixture is stirred for 18 hours. Then the reaction mixture is poured into ice water and the crystalline residue is filtered off. Yield: 8.85 g (91.6% of theory); C14H20ClN3O2 (M=297.78); calc.: molecular ion peak (M+H)+: 298/300; found: molecular ion peak (M+H)+: 298/300. the reaction mixture is stirred for 18 hours the crystalline residue is filtered off

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

Procedure: The product was obtained analogously to Example 20.1a starting from 5-(4-chlorophenyl)-2-(4-iodothiophen-2-ylethynyl)pyridine and 2-(4-methylpiperidin-1-yl)ethylamine. Yield: 3 mg (1% of theoretical); C25H26ClN3S (M=436.013); calc.: molpeak (M+H)+: 436/438 (Cl); found: molpeak (M+H)+: 436/438 (Cl); HPLC-MS: 5.10 minutes (method B). The product was obtained analogously to Example 20.1a 5.10 minutes (method B)

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

Procedure: 5.00 g (35.00 mmol) of 2-(4-methylpiperidin-1-yl)ethylamine was added under argon to a mixture of 10.39 g (35.00 mmol) of 4-bromo-1-iodo-2-methylbenzene, 0.33 g (1.75 mmol) of CuI, 30.0 g (141.00 mmol) of potassium phosphate, and 4.34 g (70.00 mmol) of ethylene glycol in 35 mL of isopropanol and the mixture was refluxed for 15 hours. The reaction mixture was evaporated down in vacuo and the residue taken up in EtOAc. The organic phase was washed with 5% aqueous ammonia, dried over magnesium sulfate, and evaporated down in vacuo. The crude product was purified by column chromatography (silica gel, EtOAc). Yield: 1.20 g (11% of theoretical); C15H23BrN2 (M=311.261); calc.: molpeak (M+H)+: 311/313 (Br); found: molpeak (M+H)+: 311/313 (Br); HPLC-MS: 4.24 minutes (method B). the mixture was refluxed for 15 hours The reaction mixture was evaporated down in vacuo The organic phase was washed with 5% aqueous ammonia dried over magnesium sulfate evaporated down in vacuo The crude product was purified by column chromatography (silica gel, EtOAc) 4.24 minutes (method B)