N-[2-(1H-indol-3-yl)ethyl]acetamide

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

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

Procedure: Tryptamine (192 mg/1.2 mmol) was initially introduced into abs. THF (5 ml), and triethylamine (179 μl/1.3 mmol) was added. Acetic anhydride (132 mg/1.3 mmol) was then added and the mixture was stirred at RT for 4 h. The mixture was concentrated to dryness i. vac. The residue was taken up in ethyl acetate and this solution was washed with saturated NaHCO3 solution (two times 20 ml) and with NaCl solution (two times 20 ml). The organic phase was dried over Na2SO4 and concentrated i. vac. The mixture was concentrated to dryness i this solution was washed with saturated NaHCO3 solution (two times 20 ml) and with NaCl solution (two times 20 ml) The organic phase was dried over Na2SO4 concentrated i

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

Procedure: Tryptamine (192 mg/1.2 mmol) was initially introduced into abs. THF (5 ml), and triethylamine (179 μl/1.3 mmol) was added. Acetic anhydride (132 mg/1.3 mmol) was then added and the mixture was stirred at RT for 4 h. The mixture was concentrated to dryness i. vac. The residue was taken up in ethyl acetate and this solution was washed with saturated NaHCO3 solution (two times 20 ml) and with NaCl solution (two times 20 ml). The organic phase was dried over Na2SO4 and concentrated i. vac. The mixture was concentrated to dryness i this solution was washed with saturated NaHCO3 solution (two times 20 ml) and with NaCl solution (two times 20 ml) The organic phase was dried over Na2SO4 concentrated i

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

Procedure: Tryptamine (192 mg/1.2 mmol) was initially introduced into abs. THF (5 ml), and triethylamine (179 μl/1.3 mmol) was added. Acetic anhydride (132 mg/1.3 mmol) was then added and the mixture was stirred at RT for 4 h. The mixture was concentrated to dryness i. vac. The residue was taken up in ethyl acetate and this solution was washed with saturated NaHCO3 solution (two times 20 ml) and with NaCl solution (two times 20 ml). The organic phase was dried over Na2SO4 and concentrated i. vac. The mixture was concentrated to dryness i this solution was washed with saturated NaHCO3 solution (two times 20 ml) and with NaCl solution (two times 20 ml) The organic phase was dried over Na2SO4 concentrated i

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 0.20 g of tert-butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-[2-(toluene-4-sulphonyloxy)ethoxy]piperidine-1-carboxylate (Example 14b) and 0.067 g of N-[2-(1H-indol-3-yl)ethyl]acetamide in 7 ml of N,N-dimethylformamide is admixed at 0° C. with 0.024 g of sodium hydride dispersion (60%) and stirred at room temperature over 20 hours. The reaction mixture is poured onto saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate (2×). The combined organic phases are washed with brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a yellow oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.35 (EtOAc); Rt=5.69. extracted with ethyl acetate (2×) The combined organic phases are washed with brine dried over sodium sulphate concentrated by evaporation

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

Procedure: The following were purchased: acetyl-CoA (Pharmacia Biotech Inc.); tryptamine-HCl, desulfo-CoA, glutathione-agarose, DTNB (Sigma); sodium phosphate, dithiothreitol, guanidinium-HCl, EDTA (Fisher Scientific); tryptophol (Aldrich); and [14C]acetyl-CoA (60 Ci/mol) (NEN Life Science Products). N-acetyltryptamine was synthesized by reacting tryptamine-HCl (500 mg, 2.5 mmol) with acetic anhydride (260 mg, 2.5 mmol) in the presence of excess triethylamine (1.75 ml). After vigorous stirring at room temperature for 50 min, the mixture was partitioned between ethyl acetate (80 ml) and water (70 ml). The organic phase was washed with saturated aqueous NaHCO3 (50 ml), 0.1 M HCl (50 ml), Na2SO4 (anhydride), and the resultant was concentrated in vacuo to afford N-acetyltryptamine as off-white crystals (88% yield). Purity (>95%) was established by TLC and 1H NMR. N-acetyltryptamine was synthesized the mixture was partitioned between ethyl acetate (80 ml) and water (70 ml) The organic phase was washed with saturated aqueous NaHCO3 (50 ml), 0.1 M HCl (50 ml), Na2SO4 (anhydride) the resultant was concentrated in vacuo

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

Procedure: Using general procedure C, 3-hydroxy-4-phenyl-cyclopent-2-enone (Lit. 17) was reacted with 1H-imidazole-2-carbaldehyde and N-[2-(1H-indol-3-yl)-ethyl]-acetamide to give the title compound as pale brown solid. MS: 455.0 ([M+H]+).

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

Procedure: Using general procedure C, 3-hydroxy-4-phenyl-cyclopent-2-enone (Lit. 17) was reacted with 3H-imidazole-4-carbaldehyde and N-[2-(1H-indol-3-yl)-ethyl]-acetamide to give the title compound as pale brown solid. MS: 455.0 ([M+H]+).

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

Procedure: Using general procedure C, 3-hydroxy-4-phenyl-cyclopent-2-enone (Lit. 17) was reacted with pyridine-3-carbaldehyde and N-[2-(1H-indol-3-yl)-ethyl]-acetamide to give the title compound as pale brown solid. MS: 466.3 ([M+H]+).

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

Procedure: Using general procedure C, 3-hydroxy-4-phenyl-cyclopent-2-enone (Lit. 17) was reacted with pyridine-2-carbaldehyde and N-[2-(1H-indol-3-yl)-ethyl]-acetamide to give the title compound as a white solid. MS: 466.3 ([M+H]+).

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

Procedure: Using general procedure C, 3-hydroxy-4-phenyl-cyclopent-2-enone (Lit. 17) was reacted with benzaldehyde and N-[2-(1H-indol-3-yl)-ethyl]-acetamide to give the title compound as a pink solid. MS: 465.0 ([M+H]+).