Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([NH:15]C(=O)OC(C)(C)C)[CH2:10][CH2:11][N:12]([CH3:14])[CH3:13])=[CH:5][CH:4]=1>C(Cl)Cl.CO>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]([NH2:15])[CH2:10][CH2:11][N:12]([CH3:14])[CH3:13])=[CH:7][CH:8]=1Hydrogen chloride (4M in dioxane, 1.132 mL, 32.61 mmol) was added to tert-butyl 1-(4-chlorophenyl)-3-(dimethylamino)propylcarbamate (Intermediate 32) (0.051 g, 0.16 mmol) in a mixture of DCM (5 mL) and methanol (2 mL) at 22° C. The resulting solution was stirred at 22° C. for 4 hours. The mixture was concentrated and the residue was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 2M NH3/MeOH and pure fractions were evaporated to dryness to afford 1-(4-chlorophenyl)-N3,N3-dimethylpropane-1,3-diamine (0.032 g, 92%) as a colourless oil.
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