5-bromopentan-2-one

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: A solution of 10 g of 5-bromo-2-pentanone in 40 cc of chloroform is added dropwise within 10 minutes to a mixture of 14.7 g of 4-(6,11-dihydrodibenzo[b,e]thiepin-11-ylidene)piperidine and 12.7 g of potassium carbonate in 200 cc of chloroform, and the mixture is heated at reflux for 18 hours. After cooling, filtration is effected, the filtrate is washed with water, dried over magnesium sulphate, and the solvent is completely removed by distillation. The oily residue is then chromatographed on 200 g of silica gel with a mixture of chloroform/ethanol 9:1, and the so purified title compound is converted into the hydrogen fumarate form. M.P. 215°-218° from ethanol. the mixture is heated at reflux for 18 hours After cooling filtration the filtrate is washed with water dried over magnesium sulphate the solvent is completely removed by distillation The oily residue is then chromatographed on 200 g of silica gel with a mixture of chloroform/ethanol 9:1 the so purified title compound

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

Procedure: A solution of 10 g of 5-bromo-2-pentanone in 40 cc of chloroform is added dropwise within 10 minutes to a mixture of 13.8 g of 4-(6,11-dihydrodibenzo[b,e]oxepin-11-ylidene)piperidine and 12.7 g of sodium carbonate in 200 cc of chloroform, and the mixture is heated at reflux for 18 hours. After cooling, filtration is effected, the filtrate is washed with water, dried over magnesium sulphate, and the solvent is completely removed by distillation. The oily residue is then chromatographed on 250 g of silica gel with a mixture of chloroform/ethanol 95:5, and the so purified title compound is converted into the hydrogen fumarate form. M.P. 228°-230°. the mixture is heated at reflux for 18 hours After cooling filtration the filtrate is washed with water dried over magnesium sulphate the solvent is completely removed by distillation The oily residue is then chromatographed on 250 g of silica gel with a mixture of chloroform/ethanol 95:5 the so purified title compound

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

Procedure: 4-(5-dibenzo[a,d]cycloheptenylidene)piperidine is reacted in a manner analogous to that described in Example 7 with 5-bromo-2-pentanone. M.P. of the hydrochloride of the title compound 206°-207° after crystallization from isopropanol. M.P. of the hydrochloride of the title compound 206°-207° after crystallization from isopropanol

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

Procedure: 9.2 g of sodium carbonate are added to a solution of 10 g of 4-(10,11-dihydro-5-dibenzo[a,d]cycloheptenylidene)piperidine in 100 cc of chloroform, a solution of 7.2 g of 5-bromo-2-pentanone in 50 cc of chloroform is then added dropwise within 20 minutes, and the mixture is subsequently boiled at reflux for 17 hours. After cooling, the precipitate is filtered off, the filtrate is extracted twice with water, dried over magnesium sulphate and concentrated by evaporation. The residue is filtered over a column of 170 g of silica gel. The fraction eluted with chloroform containing 1% of methanol is dissolved in acetone and acidifed with hydrogen chloride in ether. After the addition of more ether, the hydrochloride of the title compound crystallizes. M.P. 235°-238°. at reflux for 17 hours After cooling the precipitate is filtered off the filtrate is extracted twice with water dried over magnesium sulphate concentrated by evaporation The residue is filtered over a column of 170 g of silica gel The fraction eluted with chloroform containing 1% of methanol is dissolved in acetone After the addition of more ether the hydrochloride of the title compound crystallizes

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

Procedure: 9.2 g of sodium carbonate are added to a solution of 10 g of 4-(10,11-dihydro-5-dibenzo[a,d]cycloheptenylidene)piperidine in 100 cc of chloroform, a solution of 7.2 g of 5-bromo-2-pentanone in 50 cc of chloroform is then added dropwise within 20 minutes, and the mixture is subsequently boiled at reflux for 17 hours. After cooling, the precipitate is filtered off, the filtrate is extracted twice with water, dried over magnesium sulphate and concentrated by evaporation. The residue is filtered over a column of 170 g of silica gel. The fraction eluted with chloroform containing 1% of methanol is dissolved in acetone and acidifed with hydrogen chloride in ether. After the addition of more ether, the hydrochloride of the title compound crystallizes. M.P. 235°-238°. at reflux for 17 hours After cooling the precipitate is filtered off the filtrate is extracted twice with water dried over magnesium sulphate concentrated by evaporation The residue is filtered over a column of 170 g of silica gel The fraction eluted with chloroform containing 1% of methanol is dissolved in acetone After the addition of more ether the hydrochloride of the title compound crystallizes

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

Procedure: 7.2 g of 5-bromo-2-pentanone in 50 cc of chloroform are added dropwise to a suspension of 10.0 g of 4-(9-xanthenylidene)piperidine [M.P. 147°-149°, produced from N-methyl-4-(9-xanthenylidene)piperidine] and 9.25 g of sodium carbonate in 200 cc of chloroform. The reaction mixture is boiled at reflux for 17 hours, is filtered, concentrated by evaporation, the evaporation residue is placed on a column of 100 g of silica gel and elution is effected with chloroform containing 1% of methanol. The evaporation residue of the eluate is dissolved in acetone and made weakly acid to Congo red with hydrogen chloride in ether. The 5-[4-(9-xanthenylidene)piperidino]-2-pentanone hydrochloride which precipitates immediately is recrystallized from alcohol. M.P. 248°-251° (decomp.). at reflux for 17 hours is filtered concentrated by evaporation the evaporation residue is placed on a column of 100 g of silica gel and elution The evaporation residue of the eluate is dissolved in acetone The 5-[4-(9-xanthenylidene)piperidino]-2-pentanone hydrochloride which precipitates immediately is recrystallized from alcohol

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

Procedure: 7.2 g of 5-bromo-2-pentanone in 50 cc of chloroform are added dropwise to a suspension of 10.0 g of 4-(9-xanthenylidene)piperidine [M.P. 147°-149°, produced from N-methyl-4-(9-xanthenylidene)piperidine] and 9.25 g of sodium carbonate in 200 cc of chloroform. The reaction mixture is boiled at reflux for 17 hours, is filtered, concentrated by evaporation, the evaporation residue is placed on a column of 100 g of silica gel and elution is effected with chloroform containing 1% of methanol. The evaporation residue of the eluate is dissolved in acetone and made weakly acid to Congo red with hydrogen chloride in ether. The 5-[4-(9-xanthenylidene)piperidino]-2-pentanone hydrochloride which precipitates immediately is recrystallized from alcohol. M.P. 248°-251° (decomp.). at reflux for 17 hours is filtered concentrated by evaporation the evaporation residue is placed on a column of 100 g of silica gel and elution The evaporation residue of the eluate is dissolved in acetone The 5-[4-(9-xanthenylidene)piperidino]-2-pentanone hydrochloride which precipitates immediately is recrystallized from alcohol

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

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