1,4-dibromohexane

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

Procedure: 1-methylpiperidine (˜73.3 g), 1,4-dibromohexane (˜82 g), and dimethylformamide (˜250 mL) were combined and stirred at room temperature for about 24 hours. The solid product was filtered and then washed with diethyl ether (˜750 mL). After drying the product (˜106 g, ˜71%) was confirmed to be 1,1′-(hexane-1,6-diyl)bis(1-methylpiperidin-1-ium) bromide by 1H NMR. The solid product was filtered washed with diethyl ether (˜750 mL) After drying the product (˜106 g, ˜71%)

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

Procedure: A solution of 0.501 g (1.60 mmol) of 1-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-[1,4]diazepan-5-one (intermediate 1A) and 0.447 g (1.60 mmol) of methyl 2,5-dibromopentane in 7 ml of DMF was treated at 0° C. with 0.077 g (1.76 mmol) of NaH (55% in oil). The reaction was stirred for 20 h at RT, cooled (0° C.) and treated again with 0.224 g (0.80 mmol) of methyl 2,5-dibromopentane and 0.038 g (0.88 mmol) of NaH (55% in oil). After 1 h at 0° C. and 3 h at RT, the reaction was neutralized with cold aqueous 10% KHSO4 and extracted with Et2O (3×). The organic phases were washed with aqueous 10% KHSO4, aqueous 10% NaCl, dried over Na2SO4 evaporated and purified by flash silica gel column (CH2Cl2/Et2O 95:5 to 70:30) to yield 0.39 g (48%) of the title compound as white foam. MS: 505.1 (MH+, 1Br). cooled (0° C.) After 1 h at 0° C. 3 h at RT extracted with Et2O (3×) The organic phases were washed with aqueous 10% KHSO4, aqueous 10% NaCl dried over Na2SO4 evaporated purified by flash silica gel column (CH2Cl2/Et2O 95:5 to 70:30)

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

Procedure: 1-methylpiperidine (˜73.3 g), 1,4-dibromohexane (˜82 g), and dimethylformamide (˜250 mL) were combined and stirred at room temperature for about 24 hours. The solid product was filtered and then washed with diethyl ether (˜750 mL). After drying the product (˜106 g, ˜71%) was confirmed to be 1,1′-(hexane-1,6-diyl)bis(1-methylpiperidin-1-ium)bromide by 1H NMR. The solid product was filtered washed with diethyl ether (˜750 mL) After drying the product (˜106 g, ˜71%)

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

Procedure: 1-methylpiperidine (˜73.3 g), 1,4-dibromohexane (˜82 g), and dimethylformamide (˜250 mL) were combined and stirred at room temperature for about 24 hours. The solid product was filtered and then washed with diethyl ether (˜750 mL). After drying the product (˜106 g, ˜71%) was confirmed to be 1,1′-(hexane-1,6-diyl)bis(1-methylpiperidin-1-ium) bromide by 1H NMR. The solid product was filtered washed with diethyl ether (˜750 mL) After drying the product (˜106 g, ˜71%)