4-(chloromethyl)aniline

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 boron trichloride (100 mg) in dry benzene (5 ml), a solution of p-chloromethylaniline (100 mg) in dry benzene (2 ml) is added with cold water cooling (7°-10° C.), and the resultant mixture is refluxed for 2 hours. Then, a solution of o-chlorobenzaldehyde (99 mg) and tri-n-butylamine (131 mg) in dry benzene (2 ml) is added thereto with cold water cooling, and the mixture is stirred at room temperature for 1 hour. The reaction mixture is mixed with ice pieces and shaken with ether. The ethereal layer is washed with aqueous sodium carbonate and a saturated brine in that order, dried over potassium carbonate, and evaporated under reduced pressure. The residue is chromatographed on a column of silica gel, and the product is recrystallized from chloroform-petroleum ether to give 2-methylamino-5,2'-dichlorobenzhydrol (174 mg) as crystals melting at 106° to 108° C. The yield is 87.4%. The reaction mixture is mixed with ice pieces The ethereal layer is washed with aqueous sodium carbonate a saturated brine in that order, dried over potassium carbonate evaporated under reduced pressure The residue is chromatographed on a column of silica gel the product is recrystallized from chloroform-petroleum ether

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

Procedure: 1.1 g of 3-(4-chloromethylphenyl)-5(R)-[4-(1,2di-benzyloxycarbonylethyl)piperazinomethyl]oxazolidin-2-one [obtainable by reaction of 4-chloromethylaniline with 2,3-epoxypropan-1-ol to give N-(4-chloro-methylphenyl)-2,3-dihydroxypropylamine, reaction with diethyl carbonate in the presence of K tert-butoxide to give 3-(4-chloromethylphenyl)-5-hydroxymethyl-oxazolidin-2-one, subsequent esterification with methanesulfonyl chloride and reaction with 1-(1,2-dibenzyloxycarbonylethyl)piperazine], dissolved in 30 ml of DMF, are treated at room temperature with 0.9 g of freshly prepared guanidine, dissolved in 10 ml of DMF, and the mixture is stirred for two hours. After removal of the solvent and customary working up, 3-(4-guanidinylmethylphenyl)-5(R)-[4-(1,2-dibenzyloxycarbonylethyl)piperazinomethyl]oxazolidin-2-one is obtained. to give

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 1.2 g of 5-(1-piperazinyl)-3,4-dihydrocarbostyril, 1.17 g of potassium carbonate and 20 ml of dimethyl sulfoxide was added 650 mg of 4-aminobenzyl chloride and the mixture was stirred at 80° C. for 2.5 hours. The reaction mixture was poured into a large amount of water and extracted with chloroform. After washing with water, the extract was dried over anhydrous sodium sulfate. Chloroform was distilled off and the residue was purified through silica gel column chromatography. After conversion to hydrochloric acid salt with methanol-hydrochloric acid, the product was recrystallized from methanol-ether to give 0.4 g of 5-[4-(4-aminobenzyl)-1-piperazinyl]-3,4-dihydrocarbostyril dihydrochloride monohydrate, m.p. 224°-227° C. (decomp.), yellow granules. extracted with chloroform After washing with water the extract was dried over anhydrous sodium sulfate Chloroform was distilled off the residue was purified through silica gel column chromatography After conversion to hydrochloric acid salt with methanol-hydrochloric acid, the product was recrystallized from methanol-ether

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

Procedure: To a solution of boron trichloride (100 mg) in dry benzene (5 ml), a solution of p-chloromethylaniline (100 mg) in dry benzene (2 ml) is added with cold water cooling (7°-10° C.), and the resultant mixture is refluxed for 2 hours. Then, a solution of o-chlorobenzaldehyde (99 mg) and tri-n-butylamine (131 mg) in dry benzene (2 ml) is added thereto with cold water cooling, and the mixture is stirred at room temperature for 1 hour. The reaction mixture is mixed with ice pieces and shaken with ether. The ethereal layer is washed with aqueous sodium carbonate and a saturated brine in that order, dried over potassium carbonate, and evaporated under reduced pressure. The residue is chromatographed on a column of silica gel, and the product is recrystallized from chloroform-petroleum ether to give 2-methylamino-5,2'-dichlorobenzhydrol (174 mg) as crystals melting at 106° to 108° C. The yield is 87.4%. The reaction mixture is mixed with ice pieces The ethereal layer is washed with aqueous sodium carbonate a saturated brine in that order, dried over potassium carbonate evaporated under reduced pressure The residue is chromatographed on a column of silica gel the product is recrystallized from chloroform-petroleum ether