[isocyanato(phenyl)methyl]benzene

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

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

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

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The 3-amino-1-propanesulfonic acid (1.0 g, 7.2 mmol) was dissolved in 3N NaOH (370 mg, 9.4 mmol in 3 mL of water). After the solution was cooled to 0° C., diphenylmethyl isocyanate (1.4 mL, 7.2 mmol) was added. The reaction mixture was allowed to warm up to room temperature, stirred for 8 h (r.t.), and followed by addition of 3N NaOH (3 mL). The reaction mixture was stirred for 18 h. The pH of the reaction mixture was brought to 3 with 5N HCl. The solvent was evaporated under reduced pressure. EtOH (15 mL) was added and the mixture was stirred at reflux for 30 sec. The hot mixture was filtered. The filtrate was evaporated to dryness. This process was repeated 2 more times. The final product was dried in vacuo, affording compound AF, 837 mg (34%). to warm up to room temperature The reaction mixture was stirred for 18 h The solvent was evaporated under reduced pressure EtOH (15 mL) was added the mixture was stirred at reflux for 30 sec The hot mixture was filtered The filtrate was evaporated to dryness The final product was dried in vacuo affording compound AF, 837 mg (34%)

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

Procedure: Reagents: Benzylisothiocyanate (6.5 mmol, 0.85 mL), diphenylmethyl-isocyanate (6.5 mmol, 1.23 mL) and SO2Cl2 (6.5 mmol, 0.52 mL) in diethyl ether (25 mL). Isolation: filtration of reaction mixture. Purification: recrystallization from MeOH. Isolation: filtration of reaction mixture Purification recrystallization from MeOH

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

Procedure: To a solution of piperazin-2-one (100 mg, 1 mmol) was added (isocyanatomethylene)dibenzene (209 mg, 1 mmol) in dichloromethane (5 mL). The solution was stirred for 2 hours at room temperature and concentrated in vacuo. The residue was diluted with EtOAc and then washed consecutively with saturated aqueous NaHCO3 and brine. The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. The crude material was purified by flash column chromatography (2:98 MeOH/DCM) to give desired compound N-benzhydryl-3-oxopiperazine-1-carboxamide (Compound 1) (232 mg, 75%) as a white powder. concentrated in vacuo The residue was diluted with EtOAc washed consecutively with saturated aqueous NaHCO3 and brine The organic layer was dried (Na2SO4) filtered concentrated in vacuo The crude material was purified by flash column chromatography (2:98 MeOH/DCM)

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

Procedure: To a solution of piperazin-2-one (100 mg, 1 mmol) was added (isocyanatomethylene)dibenzene (209 mg, 1 mmol) in dichloromethane (5 mL). The solution was stirred for 2 hours at room temperature and concentrated in vacuo. The residue was diluted with EtOAc and then washed consecutively with saturated aqueous NaHCO3 and brine. The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. The crude material was purified by flash column chromatography (2:98 MeOH/DCM) to give desired compound N-benzhydryl-3-oxopiperazine-1-carboxamide (Compound 1) (232 mg, 75%) as a white powder. concentrated in vacuo The residue was diluted with EtOAc washed consecutively with saturated aqueous NaHCO3 and brine The organic layer was dried (Na2SO4) filtered concentrated in vacuo The crude material was purified by flash column chromatography (2:98 MeOH/DCM)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The 3-amino-1-propanesulfonic acid (1.0 g, 7.2 mmol) was dissolved in 3N NaOH (370 mg, 9.4 mmol in 3 mL of water). After the solution was cooled to 0° C., diphenylmethyl isocyanate (1.4 mL, 7.2 mmol) was added. The reaction mixture was allowed to warm up to room temperature, stirred for 8 h (r.t.), and followed by addition of 3N NaOH (3 mL). The reaction mixture was stirred for 18 h. The pH of the reaction mixture was brought to 3 with 5N HCl. The solvent was evaporated under reduced pressure. EtOH (15 mL) was added and the mixture was stirred at reflux for 30 sec. The hot mixture was filtered. The filtrate was evaporated to dryness. This process was repeated 2 more times. The final product was dried in vacuo, affording compound AF, 837 mg (34%). to warm up to room temperature The reaction mixture was stirred for 18 h The solvent was evaporated under reduced pressure EtOH (15 mL) was added the mixture was stirred at reflux for 30 sec The hot mixture was filtered The filtrate was evaporated to dryness The final product was dried in vacuo affording compound AF, 837 mg (34%)

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

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 a solution of 3,5-dimethyl-1-((1-methylpiperidin-4-yl)methyl)piperazine (0.2 g, 1 mmol) dissolved in methylene chloride (5 ml) was added diphenylmethyl isocyanate (0.227 g, 1.09 mmol) and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was washed with saturated sodium bicarbonate solution and brine, dried over sodium sulfate and concentrated. The residue was applied to flash column chromatography using methylene chloride and methanol (100:10) as eluents to give 0.12 g of desired product. The reaction mixture was washed with saturated sodium bicarbonate solution and brine dried over sodium sulfate concentrated