benzhydryl acetate

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: Boron trifluoride-ether complex (0.65 ml, 5.29 mmol) was added to a solution of ethyl indole-2-carboxylate (10.0 g, 52.9 mmol) in 100 ml of methylene chloride, and a solution of benzhydryl acetate (11.4 g, 50.2 mmol) in 50 ml of methylene chloride was dropwise added thereto, followed by stirring at room temperature for 40 minutes. A saturated aqueous solution of sodium bicarbonate was added to the reaction solution for neutralization followed by extraction with chloroform. The resulting organic layer was washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to give a crude product. The obtained crude product was washed with diisopropyl ether to give 15.8 g (yield: 84%) of the title compound. followed by extraction with chloroform The resulting organic layer was washed with a saturated aqueous solution of sodium bicarbonate a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate the solvent was distilled off under reduced pressure to give a crude product The obtained crude product was washed with diisopropyl ether

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

Procedure: Substantially the same procedure as in Example 263 was repeated using benzhydryl acetate (0.78 g, 3.41 mmol) and 2-(piperidinosulfonyl)indole (0.95 g, 3.59 mmol) to give 1.2 g (yield: 75%) of the title compound.

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

Procedure: To a solution of benzhydryl acetate (0.77 g, 3.39 mmol) and N,N-diethylindole-2-sulfonamide (0.9 g, 3.39 mmol) in 20 ml of methylene chloride was added methanesulfonic acid (0.7 ml, 10.7 mmol), followed by stirring at room temperature for one hour. A saturated aqueous solution of sodium bicarbonate was added to the reaction solution for neutralization followed by extraction with chloroform. The resulting organic layer was washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to give a crude product. The obtained crude product was crystallized from diisopropyl ether to give 0.99 g (yield: 67%) of the title compound. followed by extraction with chloroform The resulting organic layer was washed with a saturated aqueous solution of sodium bicarbonate a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate the solvent was distilled off under reduced pressure to give a crude product The obtained crude product was crystallized from diisopropyl ether

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

Procedure: To a solution of benzhydryl acetate (0.77 g, 3.39 mmol) and N,N-diethylindole-2-sulfonamide (0.9 g, 3.39 mmol) in 20 ml of methylene chloride was added methanesulfonic acid (0.7 ml, 10.7 mmol), followed by stirring at room temperature for one hour. A saturated aqueous solution of sodium bicarbonate was added to the reaction solution for neutralization followed by extraction with chloroform. The resulting organic layer was washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to give a crude product. The obtained crude product was crystallized from diisopropyl ether to give 0.99 g (yield: 67%) of the title compound. followed by extraction with chloroform The resulting organic layer was washed with a saturated aqueous solution of sodium bicarbonate a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate the solvent was distilled off under reduced pressure to give a crude product The obtained crude product was crystallized from diisopropyl ether

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

Procedure: Benzhydryl acetate (2.2 g, 9.71 mmol) and 2-[4-(2-chlorophenyl)piperazinylcarbonyl]indole (3.0 g, 8.83 mmol) were dissolved in a mixed solvent of methylene chloride (50 ml) and chloroform (50 ml), and methanesulfonic acid (1.72 ml, 26.5 mmol) was added thereto, followed by stirring at room temperature for 3 hours. A saturated aqueous solution of sodium bicarbonate was added to the reaction solution for neutralization followed by extraction with chloroform. The resulting organic layer was washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to give 6.5 g of a crude product. The obtained crude product was washed with ethanol (60 ml) under heating to give 4.0 g (yield: 89%) of the title compound. was added followed by extraction with chloroform The resulting organic layer was washed with a saturated aqueous solution of sodium bicarbonate a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate the solvent was distilled off under reduced pressure to give 6.5 g of a crude product The obtained crude product was washed with ethanol (60 ml) under heating

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: 108.3 g (1.05 mol; 1.05 eq) of acetic anhydride are diluted in 370 ml of dichloromethane at 20° C. The solution obtained is cooled to 0±2° C. before introducing 2.8 ml of a 96% sulphuric acid solution in a time of about 10 minutes. After stirring for about 10 minutes, 184.2 g (1 mol, 1 eq) of benzhydrol are introduced in portions at 0° C.±2° C. in 60±15 minutes. The reaction medium is maintained in contact for 2 hours at this temperature. The solution obtained The reaction medium is maintained in contact for 2 hours at this temperature

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

Procedure: Boron trifluoride-ether complex (0.65 ml, 5.29 mmol) was added to a solution of ethyl indole-2-carboxylate (10.0 g, 52.9 mmol) in 100 ml of methylene chloride, and a solution of benzhydryl acetate (11.4 g, 50.2 mmol) in 50 ml of methylene chloride was dropwise added thereto, followed by stirring at room temperature for 40 minutes. A saturated aqueous solution of sodium bicarbonate was added to the reaction solution for neutralization followed by extraction with chloroform. The resulting organic layer was washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to give a crude product. The obtained crude product was washed with diisopropyl ether to give 15.8 g (yield: 84%) of the title compound. followed by extraction with chloroform The resulting organic layer was washed with a saturated aqueous solution of sodium bicarbonate a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate the solvent was distilled off under reduced pressure to give a crude product The obtained crude product was washed with diisopropyl ether

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

Procedure: Substantially the same procedure as in Example 263 was repeated using benzhydryl acetate (0.78 g, 3.41 mmol) and 2-(piperidinosulfonyl)indole (0.95 g, 3.59 mmol) to give 1.2 g (yield: 75%) of the title compound.