3-chloro-N,N,2-trimethylpropan-1-amine

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

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

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 70 ml of dimethylformamide were suspended 4.0 g of 1-(3-hydroxyphenyl)-3-phenyl-1H-pyrazolo[3,4-b]pyridine, 2.6 g of 3-dimethylamino-2-methylpropylchloride and 2.3 g of potassium carbonate. The mixture was stirred at 100° C. for 6 hours. The solvent was distilled off under reduced pressure. By adding maleic acid, the residue was converted into the salt. The obtained crude crystals were recrystallized from a mixed solvent of ethyl acetate and ethanol to give 5.2 g of 1-[3-(3-dimethylamino-2-methylpropoxy)phenyl]-3-phenyl-1H-pyrazolo[3,4-b]pyridine·maleate, m.p. 134°-136° C. The solvent was distilled off under reduced pressure By adding maleic acid The obtained crude crystals were recrystallized from a mixed solvent of ethyl acetate and ethanol

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 70 ml of dimethylformamide were suspended 4.0 g of 1-(3-hydroxyphenyl)-3-phenyl-1H-pyrazolo[3,4-b]pyridine, 2.6 g of 3-dimethylamino-2-methylpropylchloride and 2.3 g of potassium carbonate. The mixture was stirred at 100° C. for 6 hours. The solvent was distilled off under reduced pressure. By adding maleic acid, the residue was converted into the salt. The obtained crude crystals were recrystallized from a mixed solvent of ethyl acetate and ethanol to give 5.2 g of 1-[3-(3-dimethylamino-2-methylpropoxy)phenyl]-3-phenyl-1H-pyrazolo[3,4-b]pyridine·maleate, m.p. 134°-136° C. The solvent was distilled off under reduced pressure By adding maleic acid The obtained crude crystals were recrystallized from a mixed solvent of ethyl acetate and ethanol

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 suspension of 15 g. (0.023 M) of 2,2'-dihydroxybenzil dithallium salt in 500 ml. of dry toluene was stirred vigorously while adding dropwise a solution of 8.8 g. (0.05 M) of 3-dimethylamino-2-methyl propyl chloride in 91.5 ml. of toluene. The mixture was gradually heated to reflux during the addition, and the resulting mixture was stirred and refluxed for 12 hours before a color change was observed. After cooling to 25°, the pale yellow solid was filtered off and washed with toluene. The material was resuspended in toluene and filtered off again. The combined filtrates were washed with 10% sodium hydroxide solution, saturated brine solution, and finally dried over MgSO4. Evaporation of the dry toluene extract with heating up to 70° at 11 mm resulted in an oily residue. Various salts were prepared but failed to solidify. The free base was regenerated and the crude material began to crystallize. The product was recrystallized from hexane. After cooling to +5° overnight, the material was filtered off and dried in vacuo over P2O5 and paraffin wax to obtain 3.8 g. of the title compound; m.p. 69°-70°; λKbr/max 3.55, 5.88, 6.10, 6.55, 6.72 μ. A suspension of 15 g while adding dropwise a solution of 8.8 g The mixture was gradually heated to reflux during the addition refluxed for 12 hours before a color change After cooling to 25° the pale yellow solid was filtered off washed with toluene filtered off again The combined filtrates were washed with 10% sodium hydroxide solution, saturated brine solution finally dried over MgSO4 Evaporation of the dry toluene extract with heating up to 70° at 11 mm resulted in an oily residue Various salts were prepared to crystallize The product was recrystallized from hexane After cooling to +5° overnight the material was filtered off dried in vacuo over P2O5 and paraffin wax to obtain 3.8 g

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

Procedure: To a dry, stirred suspension of 3,3'-dihydroxybenzil dithallium salt (20 g.) in toluene (250 ml.) and N,N-dimethylformamide (250 ml.) was added dropwise 104 ml. of a solution containing 48 g. of 3-dimethylamino-2-methylpropyl chloride in 500 ml. of toluene. The mixture was stirred and heated under reflux overnight. The resulting heavy white precipitate was removed and washed with toluene. The toluene solution and washings were evaporated to a syrup which was subjected to further evaporation using an oil pump vacuum. The syrup was dissolved in chloroform and applied to a column (48 × 5.2 cm) of a "dry column grade" alumina (Woelm) prepacked in chloroform. Elution was with chloroform and 500 ml. fractions (1 and 2) and 250 ml. (3-6) fractions were collected. Fractions 3-6 were pooled and evaporated to give 10.00 g. of syrup. To 7.55 g. of this material in ethanol (150 ml.) was added naphthalene-2-sulfonic acid (7.72 g.). The solution was warmed and decolorized. Evaporation and addition of seeds and ether gave the title product (9.88 g.) as the bis(2-naphthalenesulfonate) salt; m.p. 162-164°. Recrystallization with decolorization gave pure product; m.p. 164-166°. was added dropwise 104 ml of a solution containing 48 g The mixture was stirred heated under reflux overnight The resulting heavy white precipitate was removed washed with toluene The toluene solution and washings were evaporated to a syrup which was subjected to further evaporation The syrup was dissolved in chloroform dry column grade" alumina (Woelm) Elution (3-6) fractions were collected evaporated to give 10.00 g The solution was warmed Evaporation and addition of seeds and ether

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

Procedure: A suspension of 15 g. (0.023 M) of 2,2'-dihydroxybenzil dithallium salt in 500 ml. of dry toluene was stirred vigorously while adding dropwise a solution of 8.8 g. (0.05 M) of 3-dimethylamino-2-methyl propyl chloride in 91.5 ml. of toluene. The mixture was gradually heated to reflux during the addition, and the resulting mixture was stirred and refluxed for 12 hours before a color change was observed. After cooling to 25°, the pale yellow solid was filtered off and washed with toluene. The material was resuspended in toluene and filtered off again. The combined filtrates were washed with 10% sodium hydroxide solution, saturated brine solution, and finally dried over MgSO4. Evaporation of the dry toluene extract with heating up to 70° at 11 mm resulted in an oily residue. Various salts were prepared but failed to solidify. The free base was regenerated and the crude material began to crystallize. The product was recrystallized from hexane. After cooling to +5° overnight, the material was filtered off and dried in vacuo over P2O5 and paraffin wax to obtain 3.8 g. of the title compound; m.p. 69°-70°; λmaxKBr 3.55, 5.88, 6.10, 6.55, 6.72 μ. A suspension of 15 g while adding dropwise a solution of 8.8 g The mixture was gradually heated to reflux during the addition refluxed for 12 hours before a color change After cooling to 25° the pale yellow solid was filtered off washed with toluene filtered off again The combined filtrates were washed with 10% sodium hydroxide solution, saturated brine solution finally dried over MgSO4 Evaporation of the dry toluene extract with heating up to 70° at 11 mm resulted in an oily residue Various salts were prepared to crystallize The product was recrystallized from hexane After cooling to +5° overnight the material was filtered off dried in vacuo over P2O5 and paraffin wax to obtain 3.8 g

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 70 ml of dimethylformamide were suspended 4.0 g of 1-(3-hydroxyphenyl)-3-phenyl-1H-pyrazolo[3,4-b]pyridine, 2.6 g of 3-dimethylamino-2-methylpropylchloride and 2.3 g of potassium carbonate. The mixture was stirred at 100° C. for 6 hours. The solvent was distilled off under reduced pressure. By adding maleic acid, the residue was converted into the salt. The obtained crude crystals were recrystallized from a mixed solvent of ethyl acetate and ethanol to give 5.2 g of 1-[3-(3-dimethylamino-2-methylpropoxy)phenyl]-3-phenyl-1H-pyrazolo[3,4-b]pyridine·maleate, m.p. 134°-136° C. The solvent was distilled off under reduced pressure By adding maleic acid The obtained crude crystals were recrystallized from a mixed solvent of ethyl acetate and ethanol