2-bromo-1-(4-chlorophenyl)butan-1-one

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

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

Procedure: 2,4-Dihydro-4-[2-[4-(4-methoxyphenyl)-1-piperazinyl]-5-pyrimidinyl]-3H-1,2,4-triazol-3-one (0.019 mol) and N,N-dimethylformamide (200 ml) were stirred. A solution of sodium bis(trimethylsilyl)amide in tetrahydrofuran (1M) (21 ml) was added dropwise under N2 and the mixture was stirred for 30 minutes at room temperature. 2-Bromo-1-(4-chlorophenyl)-1-butanone (0.021 mol) dissolved in a little N,N-dimethylformamide was added dropwise and the mixture was stirred for 3 hours at room temperature. The mixture was poured into water and extracted with dichloromethane. The organic layer was washed with water, dried and evaporated. The residue was crystallized from 1-propanol. The precipitate was faltered off and dried in vacuo at 75° C., yielding 6 g (60%) of (±)-2-[1 -(4-chlorobenzoyl)propyl]-2,4-dihydro-4-[2-[4-(4-methoxyphenyl)-1-piperazinyl]-5-pyrimidinyl]-3H-1,2,4-triazol-3-one; mp. 184.6° C. (comp. 8). was added dropwise the mixture was stirred for 3 hours at room temperature extracted with dichloromethane The organic layer was washed with water dried evaporated The residue was crystallized from 1-propanol dried in vacuo at 75° C.

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

Procedure: 2,4-Dihydro-4-[2-[4-(4-methoxyphenyl)-1-piperazinyl]-5-pyrimidinyl]-3H-1,2,4-triazol-3-one (0.019 mol) and N,N-dimethylformamide (200 ml) were stirred. A solution of sodium bis(trimethylsilyl)amide in tetrahydrofuran (1M) (21 ml) was added dropwise under N2 and the mixture was stirred for 30 minutes at room temperature. 2-Bromo-1-(4-chlorophenyl)-1-butanone (0.021 mol) dissolved in a little N,N-dimethylformamide was added dropwise and the mixture was stirred for 3 hours at room temperature. The mixture was poured into water and extracted with dichloromethane. The organic layer was washed with water, dried and evaporated. The residue was crystallized from 1-propanol. The precipitate was faltered off and dried in vacuo at 75° C., yielding 6 g (60%) of (±)-2-[1 -(4-chlorobenzoyl)propyl]-2,4-dihydro-4-[2-[4-(4-methoxyphenyl)-1-piperazinyl]-5-pyrimidinyl]-3H-1,2,4-triazol-3-one; mp. 184.6° C. (comp. 8). was added dropwise the mixture was stirred for 3 hours at room temperature extracted with dichloromethane The organic layer was washed with water dried evaporated The residue was crystallized from 1-propanol dried in vacuo at 75° C.

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

Procedure: A mixture of 2,4-dihydro-4-[6-[4-(4-methoxyphenyl)-1-piperazinyl]-3-pyridinyl]-3H-1,2,4-triazol-3-one (0.014 mol) and sodium carbonate (0.06 mol) in methylbenzene (30 ml) and N,N-dimethylformamide (70 ml) was stirred and refluxed. 2-Bromo-1-(4-chlorophenyl)-1-butanone (0.015 mol) in trichloromethane (20 ml) was added dropwise and the mixture was stirred and refluxed with a water separator for 1 hour. The mixture was filtered warm and the tiltrate was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 98/2). The pure fractions were collected and evaporated. The residue was crystallized from 2-propanol, yielding 6 g (80%) of (±)-2-[1-(4-chlorobenzoyl)propyl]-2,4-dihydro-4-[6-[4-(4-methoxyphenyl)-1-piperazinyl]-3-pyridinyl]-3H-1,2,4-triazol-3-one; mp. 142.4° C. (comp. 1). refluxed the mixture was stirred The mixture was filtered warm the tiltrate was evaporated The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 98/2) The pure fractions were collected evaporated The residue was crystallized from 2-propanol

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

Procedure: A mixture of 2,4-dihydro-4-[6-[4-(4-methoxyphenyl)-1-piperazinyl]-3-pyridinyl]-3H-1,2,4-triazol-3-one (0.014 mol) and sodium carbonate (0.06 mol) in methylbenzene (30 ml) and N,N-dimethylformamide (70 ml) was stirred and refluxed. 2-Bromo-1-(4-chlorophenyl)-1-butanone (0.015 mol) in trichloromethane (20 ml) was added dropwise and the mixture was stirred and refluxed with a water separator for 1 hour. The mixture was filtered warm and the tiltrate was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 98/2). The pure fractions were collected and evaporated. The residue was crystallized from 2-propanol, yielding 6 g (80%) of (±)-2-[1-(4-chlorobenzoyl)propyl]-2,4-dihydro-4-[6-[4-(4-methoxyphenyl)-1-piperazinyl]-3-pyridinyl]-3H-1,2,4-triazol-3-one; mp. 142.4° C. (comp. 1). refluxed the mixture was stirred The mixture was filtered warm the tiltrate was evaporated The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 98/2) The pure fractions were collected evaporated The residue was crystallized from 2-propanol

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

Procedure: 2,4-Dihydro-4-[2-[4-(4-methoxyphenyl)-1-piperazinyl]-5-pyrimidinyl]-3H-1,2,4-triazol-3-one (0.019 mol) and N,N-dimethylformamide (200 ml) were stirred. A solution of sodium bis(trimethylsilyl)amide in tetrahydrofuran (1M) (21 ml) was added dropwise under N2 and the mixture was stirred for 30 minutes at room temperature. 2-Bromo-1-(4-chlorophenyl)-1-butanone (0.021 mol) dissolved in a little N,N-dimethylformamide was added dropwise and the mixture was stirred for 3 hours at room temperature. The mixture was poured into water and extracted with dichloromethane. The organic layer was washed with water, dried and evaporated. The residue was crystallized from 1-propanol. The precipitate was faltered off and dried in vacuo at 75° C., yielding 6 g (60%) of (±)-2-[1 -(4-chlorobenzoyl)propyl]-2,4-dihydro-4-[2-[4-(4-methoxyphenyl)-1-piperazinyl]-5-pyrimidinyl]-3H-1,2,4-triazol-3-one; mp. 184.6° C. (comp. 8). was added dropwise the mixture was stirred for 3 hours at room temperature extracted with dichloromethane The organic layer was washed with water dried evaporated The residue was crystallized from 1-propanol dried in vacuo at 75° C.

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

Procedure: A mixture of 2,4-dihydro-4-[6-[4-(4-methoxyphenyl)-1-piperazinyl]-3-pyridinyl]-3H-1,2,4-triazol-3-one (0.014 mol) and sodium carbonate (0.06 mol) in methylbenzene (30 ml) and N,N-dimethylformamide (70 ml) was stirred and refluxed. 2-Bromo-1-(4-chlorophenyl)-1-butanone (0.015 mol) in trichloromethane (20 ml) was added dropwise and the mixture was stirred and refluxed with a water separator for 1 hour. The mixture was filtered warm and the tiltrate was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 98/2). The pure fractions were collected and evaporated. The residue was crystallized from 2-propanol, yielding 6 g (80%) of (±)-2-[1-(4-chlorobenzoyl)propyl]-2,4-dihydro-4-[6-[4-(4-methoxyphenyl)-1-piperazinyl]-3-pyridinyl]-3H-1,2,4-triazol-3-one; mp. 142.4° C. (comp. 1). refluxed the mixture was stirred The mixture was filtered warm the tiltrate was evaporated The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 98/2) The pure fractions were collected evaporated The residue was crystallized from 2-propanol

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

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

Procedure: 2,4-Dihydro-4-[2-[4-(4-methoxyphenyl)-1-piperazinyl]-5-pyrimidinyl]-3H-1,2,4-triazol-3-one (0.019 mol) and N,N-dimethylformamide (200 ml) were stirred. A solution of sodium bis(trimethylsilyl)amide in tetrahydrofuran (1M) (21 ml) was added dropwise under N2 and the mixture was stirred for 30 minutes at room temperature. 2-Bromo-1-(4-chlorophenyl)-1-butanone (0.021 mol) dissolved in a little N,N-dimethylformamide was added dropwise and the mixture was stirred for 3 hours at room temperature. The mixture was poured into water and extracted with dichloromethane. The organic layer was washed with water, dried and evaporated. The residue was crystallized from 1-propanol. The precipitate was faltered off and dried in vacuo at 75° C., yielding 6 g (60%) of (±)-2-[1 -(4-chlorobenzoyl)propyl]-2,4-dihydro-4-[2-[4-(4-methoxyphenyl)-1-piperazinyl]-5-pyrimidinyl]-3H-1,2,4-triazol-3-one; mp. 184.6° C. (comp. 8). was added dropwise the mixture was stirred for 3 hours at room temperature extracted with dichloromethane The organic layer was washed with water dried evaporated The residue was crystallized from 1-propanol dried in vacuo at 75° C.

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

Procedure: A mixture of 2,4-dihydro-4-[6-[4-(4-methoxyphenyl)-1-piperazinyl]-3-pyridinyl]-3H-1,2,4-triazol-3-one (0.014 mol) and sodium carbonate (0.06 mol) in methylbenzene (30 ml) and N,N-dimethylformamide (70 ml) was stirred and refluxed. 2-Bromo-1-(4-chlorophenyl)-1-butanone (0.015 mol) in trichloromethane (20 ml) was added dropwise and the mixture was stirred and refluxed with a water separator for 1 hour. The mixture was filtered warm and the tiltrate was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 98/2). The pure fractions were collected and evaporated. The residue was crystallized from 2-propanol, yielding 6 g (80%) of (±)-2-[1-(4-chlorobenzoyl)propyl]-2,4-dihydro-4-[6-[4-(4-methoxyphenyl)-1-piperazinyl]-3-pyridinyl]-3H-1,2,4-triazol-3-one; mp. 142.4° C. (comp. 1). refluxed the mixture was stirred The mixture was filtered warm the tiltrate was evaporated The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 98/2) The pure fractions were collected evaporated The residue was crystallized from 2-propanol