N-[(4-aminophenyl)methyl]ethanesulfonamide

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 the residue of the product from step 1 (0.25 mmol) is added methanol (350 μL), hydrazine (33 μL), and Raney-Nickel (10 mg). The reaction mixture is shaken at room temperature for 16 hours, then filtered and the solution concentrated to yield ethanesulfonic acid 4-amino-benzylamide, which is used as such for the subsequent reaction. filtered the solution concentrated

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

Procedure: To the residue of the product from step 1 (0.25 mmol) is added methanol (350 μL), hydrazine (33 μL), and Raney-Nickel (10 mg). The reaction mixture is shaken at room temperature for 16 hours, then filtered and the solution concentrated to yield ethanesulfonic acid 4-amino-benzylamide, which is used as such for the subsequent reaction. filtered the solution concentrated

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

Procedure: To the residue of the product from step 1 (0.25 mmol) is added methanol (350 μL), hydrazine (33 μL), and Raney-Nickel (10 mg). The reaction mixture is shaken at room temperature for 16 hours, then filtered and the solution concentrated to yield ethanesulfonic acid 4-amino-benzylamide, which is used as such for the subsequent reaction. filtered the solution concentrated

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

Procedure: N-(4-Aminobenzyl)ethanesulfonamide (504 mg, 2.35 mmol) was dissolved in acetonitrile (3 mL) and tetrahydrofuran (4 mL). The reaction mixture was added pyridine (0.23 mL, 2.78 mmol) and phenyl chloroformate (0.31 mL, 2.43 mmol) and stirred at room temperature for 3 h under nitrogen atmosphere. TLC showed complete consumption of starting material. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic part was washed with water and brine. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The crude was purified by column chromatography to give phenyl 4-(ethylsulfonamidomethyl)phenylcarbamate (697 mg, 87%). consumption of starting material The reaction mixture was diluted with water extracted with ethyl acetate The organic part was washed with water and brine The organic layer was dried over magnesium sulfate concentrated under reduced pressure The crude was purified by column chromatography

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

Procedure: N-(4-Nitrobenzyl)ethanesulfonamide (776 mg, 3.18 mmol) was dissolved in methanol and tetrahydrofuran (1:1, 35 mL). 10% Pd/C (264 mg, 3 equiv) was added to it. The resulting mixture was stirred at room temperature for overnight under H2. TLC showed complete consumption of starting material. The mixture was filtered through celite bed and the filterate was concentrated under reduced pressure. The crude was purified by column chromatography to give N-(4-aminobenzyl)ethanesulfonamide (504 mg, 74%). consumption of starting material The mixture was filtered through celite bed the filterate was concentrated under reduced pressure The crude was purified by column chromatography