N-[4-(2-bromoethyl)phenyl]methanesulfonamide

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

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

Procedure: A mixture of potassium iodide (4.15 g, 0.025 mol), N-[4-(2-bromoethyl)phenyl]methanesulfonamide as prepared in Preparation 5 above (7.0 g, 0.025 mol), ethylheptylamine (7.16 g, 0.05 mol) and 120 ml of DMF, under N2, is allowed to stir at ambient temperature. After 18 hours the reaction mixture is concentrated under reduced pressure and the residue is combined with cold dilute NaOH. The alkaline mixture is extracted with Et2O, neutralized to pH 7 with dilute HCl and extracted with CH2Cl2. The CH2Cl2 extracts are concentrated and the residue chromatographed over silica gel with 5% MeOH-0.5% NH4OH--CH2Cl2 to give N-[4-[2-(ethylheptylamino)ethyl]phenyl]methanesulfonamide, a gum. MS calc'd for C18H32N2O2S (M+): 340.2184. Found: 340.2170. After 18 hours the reaction mixture is concentrated under reduced pressure The alkaline mixture is extracted with Et2O extracted with CH2Cl2 The CH2Cl2 extracts are concentrated the residue chromatographed over silica gel with 5% MeOH-0.5% NH4OH--CH2Cl2

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

Procedure: A mixture of potassium iodide (4.15 g, 0.025 mol), N-[4-(2-bromoethyl)phenyl]methanesulfonamide as prepared in Preparation 5 above (7.0 g, 0.025 mol), ethylheptylamine (7.16 g, 0.05 mol) and 120 ml of DMF, under N2, is allowed to stir at ambient temperature. After 18 hours the reaction mixture is concentrated under reduced pressure and the residue is combined with cold dilute NaOH. The alkaline mixture is extracted with Et2O, neutralized to pH 7 with dilute HCl and extracted with CH2Cl2. The CH2Cl2 extracts are concentrated and the residue chromatographed over silica gel with 5% MeOH-0.5% NH4OH--CH2Cl2 to give N-[4-[2-(ethylheptylamino)ethyl]phenyl]methanesulfonamide, a gum. MS calc'd for C18H32N2O2S (M+): 340.2184. Found: 340.2170. After 18 hours the reaction mixture is concentrated under reduced pressure The alkaline mixture is extracted with Et2O extracted with CH2Cl2 The CH2Cl2 extracts are concentrated the residue chromatographed over silica gel with 5% MeOH-0.5% NH4OH--CH2Cl2

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

Procedure: According to the method of Doyle and coworkers in C. T. West, et al., J. Org. Chem. 38, 2675 (1973), a stirred mixture of 4'-(2-bromoacetyl)methanesulfonanilide as prepared in Preparation 4 (6.0 g, 0.021 mol), trifluoroacetic acid (32.7 g, 0.287 mol) and triethylsilane (10.5 g, 0.0902 mol), under N2, is refluxed for 2.5 days and concentrated in vacuo. The residue is mixed with toluene, concentrated, dissolved in 1N NaOH and washed with Et2O. The aqueous layer is acidified with HCl to pH 2 and extracted well with Et2O. The combined organic extracts are dried (MgSO4) and concentrated in vacuo. The residue is chromatographed on silica gel (300 g) with 1.5% MeOH:CH2Cl2 and N-[4-(2-bromoethyl)phenyl]methanesulfonamide is crystallized from EtOAc:SSB, mp: 92°-94° C. is refluxed for 2.5 days concentrated in vacuo The residue is mixed with toluene concentrated dissolved in 1N NaOH washed with Et2O extracted well with Et2O The combined organic extracts are dried (MgSO4) concentrated in vacuo The residue is chromatographed on silica gel (300 g) with 1.5% MeOH CH2Cl2 and N-[4-(2-bromoethyl)phenyl]methanesulfonamide is crystallized from EtOAc

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

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

Procedure: A mixture of potassium iodide (4.15 g, 0.025 mol), N-[4-(2-bromoethyl)phenyl]methanesulfonamide as prepared in Preparation 5 above (7.0 g, 0.025 mol), ethylheptylamine (7.16 g, 0.05 mol) and 120 ml of DMF, under N2, is allowed to stir at ambient temperature. After 18 hours the reaction mixture is concentrated under reduced pressure and the residue is combined with cold dilute NaOH. The alkaline mixture is extracted with Et2O, neutralized to pH 7 with dilute HCl and extracted with CH2Cl2. The CH2Cl2 extracts are concentrated and the residue chromatographed over silica gel with 5% MeOH-0.5% NH4OH--CH2Cl2 to give N-[4-[2-(ethylheptylamino)ethyl]phenyl]methanesulfonamide, a gum. MS calc'd for C18H32N2O2S (M+): 340.2184. Found: 340.2170. After 18 hours the reaction mixture is concentrated under reduced pressure The alkaline mixture is extracted with Et2O extracted with CH2Cl2 The CH2Cl2 extracts are concentrated the residue chromatographed over silica gel with 5% MeOH-0.5% NH4OH--CH2Cl2

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

Procedure: According to the method of Doyle and coworkers in C. T. West, et al., J. Org. Chem. 38, 2675 (1973), a stirred mixture of 4'-(2-bromoacetyl)methanesulfonanilide as prepared in Preparation 4 (6.0 g, 0.021 mol), trifluoroacetic acid (32.7 g, 0.287 mol) and triethylsilane (10.5 g, 0.0902 mol), under N2, is refluxed for 2.5 days and concentrated in vacuo. The residue is mixed with toluene, concentrated, dissolved in 1N NaOH and washed with Et2O. The aqueous layer is acidified with HCl to pH 2 and extracted well with Et2O. The combined organic extracts are dried (MgSO4) and concentrated in vacuo. The residue is chromatographed on silica gel (300 g) with 1.5% MeOH:CH2Cl2 and N-[4-(2-bromoethyl)phenyl]methanesulfonamide is crystallized from EtOAc:SSB, mp: 92°-94° C. is refluxed for 2.5 days concentrated in vacuo The residue is mixed with toluene concentrated dissolved in 1N NaOH washed with Et2O extracted well with Et2O The combined organic extracts are dried (MgSO4) concentrated in vacuo The residue is chromatographed on silica gel (300 g) with 1.5% MeOH CH2Cl2 and N-[4-(2-bromoethyl)phenyl]methanesulfonamide is crystallized from EtOAc