N-ethyl-N-(piperidin-2-ylmethyl)ethanamine

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:; See reaction.notes.procedure_details.

Procedure: Prepared analogously to Example (1b) from 5,11-dihydro-11-(prop-2-ynyl)-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one, paraformaldehyde and 2-[(diethylamino)methyl]piperidine in a yield of 28% of theory. Colourless crystals, m.p. 132°-134° C.

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

Procedure: 5.6 g (0.0174 mole) of 9-chloro-11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one were suspended in 100 ml of anhydrous dioxane and, after addition of 6.0 g (0.035 mol) of 2-[(diethylamino)methyl]piperidine, the mixture was boiled under reflux for 12 hours. under reflux for 12 hours

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

Procedure: Prepared in analogy to Example 2 from 11-(chloroacetyl)-5,11-dihydro-8-methyl-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one and 2-[(diethylamino)methyl]piperidine, but using acetonitrile as solvent, in a yield of 54% of theory. M.p. 173-174° C. (diisopropylether).

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

Procedure: Prepared in analogy to Example 2 from 11-(chloroacetyl)-5,11-dihydro-8-methyl-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one and 2-[(diethylamino)methyl]piperidine, but using acetonitrile as solvent, in a yield of 54% of theory. M.p. 173-174° C. (diisopropylether).

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 125 g (0.388 mole) of 9-chloro-11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]-benzodiazepin-6-one, 2480 ml of dry dimethyl formamide, 73.0 g (0.429 mole) of D,L-2-[(diethylamino)methyl]piperidine, 60 ml (0.429 mole) of anhydrous triethylamine and 3.0 g of sodium iodide was stirred at an internal temperature of 50° C. for 32 hours and then at room temperature for 15 hours. Insolubles were removed by filtration, and the filtrate was evaporated at the oil pump and at a bath temperature of 45° C. The remaining product was dissolved in 5% hydrochloric acid, and the solution was extracted by shaking twice with 50 ml of dichloromethane each time. The aqueous layer was made alkaline by addition of concentrated potassium carbonate solution, and the liberated base was taken up in dichloromethane, and the solution was treated with 2 g of active charcoal and dried over sodium sulphate. The dark oil remaining after the solvent had been removed by evaporation was purified by column chromatography on 800 g of silica gel (35-70 mesh) using dichloro- methane/methanol/ethyl acetate/cyclohexane/concentrated ammonia 59/7.5/25/7.5/1 (v/v) for elution. The fractions containing the compound which was sought (132 g) were dissolved in dilute aqueous maleic acid solution. The filtered solution was washed four times with 50 ml of ethyl acetate each time, and was then saturated with solid potassium carbonate and exhaustively extracted with dichloromethane. The combined dichloromethane phases were dried over sodium sulphate and evaporated, and 109 g of a partially crystallised oil remained. After recrystallisation twice from 450 ml of acetonitrile each time, using 2 g of active charcoal each time, 63.0 g (36% of theory) of colourless crystals of m.p. 167.5-169° C. were obtained. at room temperature for 15 hours Insolubles were removed by filtration the filtrate was evaporated at the oil pump and at a bath temperature of 45° C The remaining product was dissolved in 5% hydrochloric acid the solution was extracted by shaking twice with 50 ml of dichloromethane each time by addition of concentrated potassium carbonate solution the solution was treated with 2 g of active charcoal dried over sodium sulphate had been removed by evaporation was purified by column chromatography on 800 g of silica gel (35-70 mesh) for elution The fractions containing the compound which were dissolved in dilute aqueous maleic acid solution The filtered solution was washed four times with 50 ml of ethyl acetate each time saturated with solid potassium carbonate and exhaustively extracted with dichloromethane The combined dichloromethane phases were dried over sodium sulphate evaporated After recrystallisation twice from 450 ml of acetonitrile each time were obtained

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

Procedure: The title compound is prepared analogously to Example 2 from 11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one and (+)-2-[(diethylamino)methyl]piperidine to give colorless crystals, mp. 210°-211.5° C. (n-propanol/activated charcoal): [α]D20 =-12° (dilute aqueous hydrochloride acid).

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

Procedure: The title compound is prepared analogously to Example 2 from 11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one and (+)-2-[(diethylamino)methyl]piperidine to give colorless crystals, mp. 210°-211.5° C. (n-propanol/activated charcoal): [α]D20 =-12° (dilute aqueous hydrochloride acid).