4,5,6, and 7-indole and indoline derivatives, their preparation and use
a technology of in which is applied in the field of 4, 5, 6, and 7indole and indoline derivatives, their preparation and, can solve the problems of patients withdrawing from treatment, ssri's and all other antidepressants currently available, and significant late onset of action, and achieve the effect of inhibiting the activity of potent serotonin
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example 1
[0240] 1a. 1-(2-(3-Benzofuranyl)ethyl)-4-(1H-indol-4-yl)piperazine, oxalate
[0241] A mixture of 2-(3-benzofuranyl)acetic acid (0.95 g), 1-(1H-indol-4-yl)piperazine (1.3 g), and N,N-dicyclohexylcarbodiimide (1.3 g) in a mixture of dry tetrahydrofuran (50 mL) and dry dimethylformamide (10 mL) was stirred for 16 h at room temperature. Filtration and removal of solvent in vacuo gave an oil which was purified by flash chromatography (eluent: ethyl acetate / heptane / triethylamine 10:9:1) giving 1-(3-benzofuranyl)methylcarbonyl-4-(1H-indol-4-yl)piperazi- ne (0.5 g) as an oil.
[0242] The oil was dissolved in tetrahydrofuran (20 mL) and treated with a suspension of lithium aluminium hydride (0.26 g) in tetrahydrofuran (20 mL) at room temperature under a nitrogen atmosphere followed by reflux for 4 hours. The reaction mixture was cooled to 0.degree. C. and treated subsequently with water (1 mL), 15% aq. sodium hydroxide (0.5 mL), and water (2.5 mL). After stirring for 30 min the mixture was filte...
example 2
[0265] 2a. 1-(2-(6-Chloro-1H-indol-3-yl)ethyl)-4-(1H-indol-4-yl)piperazine- , oxalate
[0266] A solution of 6-chloro-1H-indole (15 g) in diethyl ether (300 mL) was cooled to 0.degree. C. and treated with a solution of oxalyl chloride (9.4 mL) in diethyl ether (30 mL). The mixture was stirred for 16 hours at room temperature. Filtration gave 2-(6-chloro-1H-indol-3-yl)-2-oxoacet- yl chloride as a crystalline material (15.5 g). A part of this product (2.5 g) was dissolved in dry tetrahydrofuran (25 mL) and added dropwise to a solution of 1-(1H-indol-4-yl)piperazine (1.4 g) and triethylamine (15 mL) in tetrahydrofuran (100 mL). After stirring for 16 hours the reaction mixture was concentrated in vacuo. The remaining oil was purified by flash chromatography (eluent: ethyl acetate / methanol / triethyl- amine 85:10:5) giving 1-(2-(6-chloro-1H-indol-3-yl)-1,2-dioxoethyl)-4-(1H-- indol-4-yl)piperazine (1.6 g) as a crystalline material. This product was suspended in tetrahydrofuran (25 mL) and add...
example 3
[0302] 3a, 1-(2-(5-Fluoro-1H-indol-3-yl)ethyl)-4-(6-hydroxymethyl-1H-indol- -4-yl)piperazine
[0303] A solution of 1-(2-(5-fluoro-1H-indol-3-yl)-I,2-dioxoethyl)-4-(6-me- thoxycarbonyl-1H-indol-4-yl)piperazine (1.8 g, prepared from 2-(5-fluoro-1H-indol-3-yl)-2-oxoacetyl chloride and 1-(6-methoxycarbonyl-1H-indol-4-yl)piperazine by the procedure described in Example 2) in tetrahydrofuran (50 mL) was added dropwise to a suspension of lithium aluminium hydride (1.7 g) in tetrahydrofuran (125 mL) at room temperature followed by reflux for 4 hours. The reaction mixture was cooled to 5.degree. C. followed by subsequent addition of water (3.4 mL), 15% aq. sodium hydroxide (1.7 mL), and water (8.5 mL). Filtration and removal of solvent in vacuo gave an oil which was purified by flash chromatography (eluent: ethyl acetate / methanol / triethylamine 85:10:5) giving the title product (0.9 g), which was crystallized from diisopropyl ether. Mp 198-200.degree. C. .sup.1H-NMR (DMSO-d.sub.6): 2.60-2.80 (m...
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