2-(1H-indol-3-yl)-N-methylethanamine

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: 1.78 g of N-methyl-tryptamine (i.e., 3-(2-methylaminoethyl)-indole) and 3.1 g of 4,4-bis(ethoxycarbonyl)-butanal were treated in the same manner as described in Example 21-(1). 2.1 g of 1,2,3,4-tetrahydro-1-[3,3-bis-(ethoxycarbonyl)propyl]-2-methyl-β-carboline were thereby obtained. Yield: 55.0%

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6.6 g of glutaric acid were added to 8.70 g of N-methyl-tryptamine (i.e., 3-(2-methylaminoethyl)-indole), and the mixture was heated at 150° C. under reduced pressure for 2 hours. After the reaction was completed, the product was recrystallized from a mixture of ethyl acetate and n-hexane. 10.8 g of N-methyl-N-(4-carboxybutyryl)-tryptamine (i.e., 3-[2-(N-methyl-4-carboxybutanamido)ethyl]-indole) were thereby obtained. M.p. 125°-126° C. Yield: 75.0% the product was recrystallized from a mixture of ethyl acetate and n-hexane

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

Procedure: 8.70 g of N-methyl-tryptamine (i.e., 3-(2-methylaminoethyl)-indole) were dissolved in 100 ml of benzene, and 5.7 g of glutaric acid anhydride were added thereto. The mixture was stirred at 80° C. for 3 hours. After the reaction was completed, the mixture was evaporated to remove solvent. 12.0 g of N-methyl-N-(4-carboxybutyryl)-tryptamine (i.e., 3-[2-(N-methyl-4-carboxybutanamido)ethyl]-indole) were thereby obtained. Yield: 90% the mixture was evaporated to remove solvent

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

Procedure: 8.70 g of N-methyl-tryptamine (i.e., 3-(2-methylaminoethyl)-indole) were dissolved in 100 ml of benzene, and 5.7 g of glutaric acid anhydride were added thereto. The mixture was stirred at 80° C. for 3 hours. After the reaction was completed, the mixture was evaporated to remove solvent. 12.0 g of N-methyl-N-(4-carboxybutyryl)-tryptamine (i.e., 3-[2-(N-methyl-4-carboxybutanamido)ethyl]-indole) were thereby obtained. Yield: 90% the mixture was evaporated to remove solvent

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 8.0 g of dimethyl glutarate were added to 8.70 g of N-methyl-tryptamine (i.e., 3-(2-methylaminoethyl)-indole), and the mixture was heated at 150° C. under reduced pressure for 2 hours. After the reaction was completed, the mixture was acidified with dilute hydrochloric acid and then extracted with ethyl acetate. The extract was washed with water, an aqueous saturated sodium bicarbonate solution and an aqueous saturated sodium chloride solution, successively. The washed extract was dried and evaporated under reduced pressure to remove solvent. The residue thus obtained was recrystallized from a mixture of ethyl acetate and n-hexane. 11.3 g of N-methyl-N-(4-methoxycarbonylbutyryl)-tryptamine (i.e., 3-[2-(N-methyl-4-methoxycarbonylbutanamido)ethyl]-indole) were thereby obtained. M.p. 101°-102° C. Yield: 70% extracted with ethyl acetate The extract was washed with water The washed extract was dried evaporated under reduced pressure to remove solvent The residue thus obtained was recrystallized from a mixture of ethyl acetate and n-hexane

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

Procedure: 10.3 g of N-methyl-tryptamine (i.e., 3-(2-methylaminoethyl)-indole) and 11.7 g of 4-methoxycarbonylbutyryl chloride were treated in the same manner as described in Example 1. 16.6 g of N-methyl-N-(4-methoxycarbonylbutyryl)-tryptamine (i.e., 3-[2-(N-methyl-4-methoxycarbonylbutanamido)ethyl]indole) were therby obtained. Yield: 92.8%

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

Procedure: 10.3 g of N-methyl-tryptamine (i.e., 3-(2-methylaminoethyl)-indole) and 11.7 g of 4-methoxycarbonylbutyryl chloride were treated in the same manner as described in Example 1. 16.6 g of N-methyl-N-(4-methoxycarbonylbutyryl)-tryptamine (i.e., 3-[2-(N-methyl-4-methoxycarbonylbutanamido)ethyl]indole) were therby obtained. Yield: 92.8%

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

Procedure: Using 3-(2-methylaminoethyl)indole (123 mg, 0.70 mmol) and 1-(3-chloropropyl)piperidine hydrochloride (198 mg, 1.0 mmol) instead of 4-(3-indolyl)piperidine and 1-(3-chloropropyl)-3-(4-methoxyphenyl)piperidine hydrochloride respectively, reaction and concentration were carried out in the same procedure as Example 2. The resulting crude product was purified by column chromatography on a silica gel (silica gel NH-DM 1020 produced by Fuji Silysia Chemical Ltd., eluent; hexane:ethyl acetate=1:1) to afford a free form (166 mg) of the title compound as a pale yellow viscous oil. After adding hydrochloric acid/methanol to a solution of the free form in methanol, the mixture was concentrated and was then reprecipitated with methanol/ether to afford the title compound (167 mg, yield: 64%) as a pale yellow crystalline powder. reaction and concentration The resulting crude product was purified by column chromatography on a silica gel (silica gel NH-DM 1020 produced by Fuji Silysia Chemical Ltd., eluent; hexane:ethyl acetate=1:1)