Reaction SMILES: [CH2:1]([N:8]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:9]1[CH2:14][CH2:13][CH:12]([NH:15][CH3:16])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>C(Cl)Cl>[CH2:17]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:9]1[CH2:14][CH2:13][CH:12]([N:15]([CH3:16])[S:25]([CH3:24])(=[O:27])=[O:26])[CH2:11][CH2:10]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
Reactant: CNC1CCC(N(Cc2ccccc2)Cc2ccccc2)CC1
Reactant: CS(=O)(=O)Cl
Solvent: ClCCl
Product: CN(C1CCC(N(Cc2ccccc2)Cc2ccccc2)CC1)S(C)(=O)=O

Procedure:
1-(t-Butoxycarbonyl)-amino-4-aminocyclohexane (21.4 g, 0.1 mol) and Cs2CO3 (71.7 g, 0.22 mol) were stirred in acetonitrile (500 mL) on an ice bath under Ar. Benzyl bromide (26 mL, 0.22 mol) in acetonitrile (20 mL) was then added dropwise, the reaction mixture was then allowed to warm to RT and was stirred overnight. The reaction mixture was then diluted with EtOAc, washed with water (×2) and brine, dried over sodium sulfate, filtered, and dried in vacuo to provide the dibenzyl derivative. The product was then dissolved in dry THF added via cannula under Ar, stirred initially at RT and then cooled to 0° C. using an ice bath prior to the portionwise addition of NaH (8 g, 60%), and was allowed to stir at 0° C. for 25 min. CH3I (18 mL) in THF (7 mL) was then added dropwise over 15 min. The reaction mixture was allowed to stir at RT overnight. The reaction mixture was then cooled on an ice bath and NaH (2 g) was added portionwise and allowed to stir for 45 min. CH3I (4.5 mL) was then added and the mixture allowed to stir and reach RT The reaction was then slowly quenched with water. The reaction mixture was then diluted with EtOAc, washed with water (×2) and brine, dried over sodium sulfate, filtered, and dried in vacuo and purified on silica column with 0% to 60% EtOAc/hexane to yield 1-[N-(t-butoxycarbonyl)-N-methyl-amino]-4-(N′,N′-dibenzyl-amino)-cyclohexane (35 g, 0.086 mol). This was then stirred in MeOH (675 mL) at RT under Ar. HCl (675 mL, 2 N) was then added and allowed to stir for approximately 5 hours. After concentrating in vacuo, the mixture was poured into saturated NaHCO3 and the organic phase extracted into DCM. NaOH (2 N aq) was added to the aqueous layer until basic, and the organic layer was then extracted into DCM (×3), washed with brine and dried over sodium sulfate, filtered and solvent removed in vacuo to yield N,N-dibenzyl-N′-methyl-cyclohexane-1,4-diamine (23.02 g). TEA (39 mL) was added to the N,N-dibenzyl-N′-methyl-cyclohexane-1,4-diamine (23 g) in DCM (500 mL) under Ar. The reaction was then cooled on an ice bath and MsCl (7.25 mL) was added dropwise and allowed to stir and reach RT. The reaction was then diluted with DCM, washed with NaHCO3, water, and brine, and filtered and dried over sodium sulfate to yield N-(4-dibenzylamino-cyclohexyl)-N-methyl-methanesulfonamide (25.14 g). This was mixed with Pd(OH)2 (17 g, 20%) in EtOH (650 mL abs). Acetic acid (9.3 mL) was then added and H2 was added over 3.5 hours and the reaction allowed to stir overnight. The product was concentrated in vacuo and then stirred overnight in EtOAc, filtered, washed with ether, and the solvent removed in vacuo at 45° C. for 2 days to yield N-(4-amino-cyclohexyl)-N-methyl-methanesulfonamide (12.03 g).