3-bromo-N,N-diethylpropan-1-amine

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:

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:

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

Procedure: To 60 ml of anhydrous N,N-dimethylformamide were added 7.50 g of the 1-(3-dimethylaminobutyl)-3-aminoindazole, 8.98 g of 3-bromopropyldiethylamine hydr bromide and 7.89 g of anhydrous potassium carbonate, and the mixture was stirred for 12 hours at 80° C. After cooling, the mixture was added with 80 ml of water and extracted with diethyl ether. The diethyl ether layer was extracted three times with 2N hydrochloric acid, and the hydrochlor.ic acid layer was washed with diethyl ether. The pH of the layer was adjusted to at least 11 with potassium carbonate, and the alkali layer was extracted three times with chloroform. The chloroform layer was dried over anhydrous sodium sulfate, and chloroform was removed under reduced pressure. The residue thus obtained was subjected to an alumina-column chromatography (alumina: 200 g) using chloroform as the developing solvent to give 6.18 g of 1-(3-dimethylaminobutyl)-3-(3-diethylaminopropylamino)indazole having the following analytical values in a yield of 52%. After cooling extracted with diethyl ether The diethyl ether layer was extracted three times with 2N hydrochloric acid the hydrochlor.ic acid layer was washed with diethyl ether the alkali layer was extracted three times with chloroform The chloroform layer was dried over anhydrous sodium sulfate, and chloroform was removed under reduced pressure The residue thus obtained

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

Procedure: To 60 ml of anhydrous N,N-dimethylformamide were added 7.50 g of the 1-(3-dimethylaminobutyl)-3-aminoindazole, 8.98 g of 3-bromopropyldiethylamine hydr bromide and 7.89 g of anhydrous potassium carbonate, and the mixture was stirred for 12 hours at 80° C. After cooling, the mixture was added with 80 ml of water and extracted with diethyl ether. The diethyl ether layer was extracted three times with 2N hydrochloric acid, and the hydrochlor.ic acid layer was washed with diethyl ether. The pH of the layer was adjusted to at least 11 with potassium carbonate, and the alkali layer was extracted three times with chloroform. The chloroform layer was dried over anhydrous sodium sulfate, and chloroform was removed under reduced pressure. The residue thus obtained was subjected to an alumina-column chromatography (alumina: 200 g) using chloroform as the developing solvent to give 6.18 g of 1-(3-dimethylaminobutyl)-3-(3-diethylaminopropylamino)indazole having the following analytical values in a yield of 52%. After cooling extracted with diethyl ether The diethyl ether layer was extracted three times with 2N hydrochloric acid the hydrochlor.ic acid layer was washed with diethyl ether the alkali layer was extracted three times with chloroform The chloroform layer was dried over anhydrous sodium sulfate, and chloroform was removed under reduced pressure The residue thus obtained

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

Procedure: 2.6 gm of a 55% suspension of sodium hydride in oil were added in portions to a mixture of 5.1 gm of 7,7-dimethyl-2-phenyl-5H,7H-imidazo[4,5-h]isoquinoline-4,6-dione hydrochloride and 50 ml of dimethyl sulfoxide. After stirring the mixture at room temperature for one hour, 4.8 gm of 3-diethylamino propyl bromide hdyrobromide were added, and the mixture was heated at 50° C. for 3 hours. The reaction mixture was admixed with water and extracted several times with chloroform. The chloroform phases were evaporated and the residue was purified on a silicagel column. The dihydrochloride was precipitated from acetone with ethereal hydrochloric acid and recrystallized from methanol/acetone. the mixture was heated at 50° C. for 3 hours extracted several times with chloroform The chloroform phases were evaporated the residue was purified on a silicagel column The dihydrochloride was precipitated from acetone with ethereal hydrochloric acid recrystallized from methanol/acetone

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