2-ethylpiperidine

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:0.00; pressure:0.00; stir:

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5-bromo-2-fluorobenzaldehyde (20 g, 0.099 mol) in dimethyl sulfoxide (230 mL) and water (70 mL), were added 2-ethylpiperidine (14.4 mL, 0.1083 mol) and sodium carbonate (20.88 g, 0.197 mol). The resulting mixture was heated at 110° C. for a period of 30 h. The reaction mixture was cooled to room temperature, diluted with water (1000 mL), extracted by methyl tert-butyl ether (2×500 mL), dried using sodium sulphate and concentrated under reduced pressure. The resulting crude was purified by column chromatography on silica gel (60-120 mesh) using pet ether as eluent to afford the titled compound as a yellow liquid. 1H NMR (DMSO-d6, 400 MHz) δ 10.15 (1H, s), 7.70-7.73 (2H, d), 7.22-7.25 (1H, m), 3.08-3.13 (2H, m), 2.84-2.86 (1H, m), 1.83-1.84 (1H, m), 1.34-1.67 (7H, m), 0.62-0.66 (3H, t). The reaction mixture was cooled to room temperature extracted by methyl tert-butyl ether (2×500 mL) dried concentrated under reduced pressure The resulting crude was purified by column chromatography on silica gel (60-120 mesh)

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

Procedure: 8.5 gm (0.027 mol) of 5-(3-chloro-propionyl)-5,10-dihydro-10-methyl-11H-dibenzo[b,e][1,4]diazepin-11-one and 8.5 gm (0.075 mol) of 2-ethyl-piperidine were refluxed in 85 ml of n-propanol for 3 hours, and the reaction mixture was worked up as described in Example 10. After recrystallization from a mixture consisting of equal parts of dioxane and acetone, 6.8 gm of the hydrochloride were obtained. After recrystallization from a mixture

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

Procedure: 143 g (0.5 mole) of β-(2-methyl-6-phenyl-imidazo[2,1-b]-1,3,4-thiadiazol-5-yl)-propenoic acid were suspended in 1.5 liters of absolute toluene at 60° to 70° C. 50 ml of thionyl chloride were added dropwise, a clear solution resulting. The solution was then heated under reflux for 2 hours and subsequently cooled to room temperature. 220 ml (1.5 moles) of 2-ethylpiperidine were next added dropwise and the mixture was boiled under reflux for one hour. The cooled mixture was filtered (the residue was discarded) and the filtrate was extracted twice with 300 ml of water. The toluene phase was dried over sodium sulphate and filtered and the filtrate was concentrated by distillation. The residue was recrystallised from 400 ml of ethyl acetate. a clear solution resulting The solution was then heated under reflux for 2 hours under reflux for one hour The cooled mixture was filtered (the residue was extracted twice with 300 ml of water The toluene phase was dried over sodium sulphate filtered the filtrate was concentrated by distillation The residue was recrystallised from 400 ml of ethyl acetate