1-N,1-N-diethylpentane-1,4-diamine

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: To a vigorously stirred mixture containing 970 g. (6.2 moles) of freshly distilled N1,N1 -diethyl-1,4 pentanediamine, 4 l. of 1,2-dichloroethane and 1 l. of water at 5°-10° C. there was simultaneously added dropwise a solution containing 5.95 moles of 4-chloro-2-nitrobenzoyl chloride in approximately 8 l. of 1,2-dichloroethane and a solution containing 410 g. (6.2 moles) of 85% potassium hydroxide in 1 l. of water. When the addition was complete the ice bath was removed and stirring was continued 0.5 hours at room temperature. The organic layer was separated, dried over anhydrous calcium sulfate and evaporated to dryness under vacuum. The residue was dissolved in 3 l. or 1,2-dichloroethane and the resulting solution was treated with decolorizing carbon and filtered. The filtrate was diluted to 6 l. with additional 1,2-dichloroethane to give a pale yellow solution of 4-choro-N-[4-(diethylamino)-1-methylbutyl]-2-nitrobenzamide which was divided into three equal portions which were used directly in the next step. To a vigorously stirred mixture containing 970 g When the addition was removed The organic layer was separated dried over anhydrous calcium sulfate evaporated to dryness under vacuum The residue was dissolved in 3 l or 1,2-dichloroethane and the resulting solution was treated with decolorizing carbon filtered The filtrate was diluted to 6 l

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

Procedure: To a vigorously stirred mixture containing 970 g. (6.2 moles) of freshly distilled N1,N1 -diethyl-1,4 pentanediamine, 4 l. of 1,2-dichloroethane and 1 l. of water at 5°-10° C. there was simultaneously added dropwise a solution containing 5.95 moles of 4-chloro-2-nitrobenzoyl chloride in approximately 8 l. of 1,2-dichloroethane and a solution containing 410 g. (6.2 moles) of 85% potassium hydroxide in 1 l. of water. When the addition was complete the ice bath was removed and stirring was continued 0.5 hours at room temperature. The organic layer was separated, dried over anhydrous calcium sulfate and evaporated to dryness under vacuum. The residue was dissolved in 3 l. or 1,2-dichloroethane and the resulting solution was treated with decolorizing carbon and filtered. The filtrate was diluted to 6 l. with additional 1,2-dichloroethane to give a pale yellow solution of 4-choro-N-[4-(diethylamino)-1-methylbutyl]-2-nitrobenzamide which was divided into three equal portions which were used directly in the next step. To a vigorously stirred mixture containing 970 g When the addition was removed The organic layer was separated dried over anhydrous calcium sulfate evaporated to dryness under vacuum The residue was dissolved in 3 l or 1,2-dichloroethane and the resulting solution was treated with decolorizing carbon filtered The filtrate was diluted to 6 l

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

Procedure: 2.47 g of 1,3-bis[[p-(dimethylamino)benzylidene]amino]-2-(methylthio)imidazolium tetrafluoroborate are suspended in 50 ml of absolute acetonitrile, whereupon the suspension is treated with 7.8 g of absolute 2-amino-5-(diethylamino)pentane. The mixture is stirred at room temperature under an argon atmosphere for about 24 hours. The insoluble constituents are removed by filtration and the filtrate is treated with 450 ml of diethyl ether. The pale yellow precipitate obtained is removed by filtration under suction, washed three times with diethyl ether and recrystallized from methanol/diethyl ether. There is obtained pale yellow 1,3-bis[[p-(dimethylamino) benzylidene]amino]-2-[[4-(diethylamino)-1-methylbutyl]amino]imidazolium tetrafluoroborate of melting point 187°-191° (decomposition). The insoluble constituents are removed by filtration the filtrate is treated with 450 ml of diethyl ether The pale yellow precipitate obtained is removed by filtration under suction washed three times with diethyl ether recrystallized from methanol/diethyl ether

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

Procedure: 2.47 g of 1,3-bis[[p-(dimethylamino)benzylidene]amino]-2-(methylthio)imidazolium tetrafluoroborate are suspended in 50 ml of absolute acetonitrile, whereupon the suspension is treated with 7.8 g of absolute 2-amino-5-(diethylamino)pentane. The mixture is stirred at room temperature under an argon atmosphere for about 24 hours. The insoluble constituents are removed by filtration and the filtrate is treated with 450 ml of diethyl ether. The pale yellow precipitate obtained is removed by filtration under suction, washed three times with diethyl ether and recrystallized from methanol/diethyl ether. There is obtained pale yellow 1,3-bis[[p-(dimethylamino) benzylidene]amino]-2-[[4-(diethylamino)-1-methylbutyl]amino]imidazolium tetrafluoroborate of melting point 187°-191° (decomposition). The insoluble constituents are removed by filtration the filtrate is treated with 450 ml of diethyl ether The pale yellow precipitate obtained is removed by filtration under suction washed three times with diethyl ether recrystallized from methanol/diethyl ether

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

Procedure: 19.116 millimols, i.e. a yield of 94.9% relative to the 7-chloro-1,2,3,4-tetrahydroquinolin-4-one converted, and a yield of 97.5% relative to the 1-diethylamino-4-amino-pentane converted, and

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

Procedure: 3.665 millimols, i.e. a yield of 90% relative to the 7-chloro-1,2,3,4-tetrahydroquinolinone converted, and a yield of 91.2% relative to the 1-diethylamino-4-aminopentane converted, and

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

Procedure: 17.904 millimols, i.e. a yield of 98.05% relative to the 7-chloro-1,2,3,4-tetrahydroquinolin-4-one converted, and a yield of 96.86% relative to the 1-diethylamino-4-amino-pentane converted, and

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

Procedure: 17.904 millimols, i.e. a yield of 98.05% relative to the 7-chloro-1,2,3,4-tetrahydroquinolin-4-one converted, and a yield of 96.86% relative to the 1-diethylamino-4-amino-pentane converted, and

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

Procedure: 17.8 millimols, representing a yield (determined) of 99% relative to the 7-chloro-1,2,3,4-tetrahydroquinolin-4-one converted, and of 96.3% relative to the 1-diethylamino-4-aminopentane converted, and

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

Procedure: The procedure was carried out as described previously in step (b) of Example 8 with Compound 7 (1.9 g, 9.3 mmol), 2-succinimido-1,1,3,3-tetramethyluronium tetrafluoroborate (3.4 g, 11.2 mmol), N,N-diisopropyl ethylamine (3.4 mL, 19.5 mmol), 2-amino-5-diethylaminopentane (2.2 g, 13.9 mmol) and DMF (40 mL). Compound 10 was obtained (2.64 g) as a viscous liquid and used without any further purification. The structure of Compound 10 is given below: