2-(2-methylpiperidin-1-yl)ethanamine

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

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

Procedure: 15 mg (12%) of the target compound was obtained in the same manner of Example 1, using 3-(4-chloro-benzyl)-2,4-dioxoquinazoline-7-carboxylic acid (90 mg, 0.272 mol) obtained in Example 1 and 2-(2-methyl-piperidine-1-yl)-ethylamine (77 mL, 0.544 mmol).

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

Procedure: 15 mg (12%) of the target compound was obtained in the same manner of Example 1, using 3-(4-chloro-benzyl)-2,4-dioxoquinazoline-7-carboxylic acid (90 mg, 0.272 mol) obtained in Example 1 and 2-(2-methyl-piperidine-1-yl)-ethylamine (77 mL, 0.544 mmol).

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

Procedure: A solution of DCM containing 4-(2-phenyl-4,5,6,7-tetrahydro-1H-indol-1-yl)benzoic acid (Intermediate 7, 1 eq.) was stirred at room temperature, DMAP (1.1 equivalent) and 2-(2-methylpiperidin-1-yl)ethanamine (1 eq.) were added. The reaction mixture was then cooled down to 0° C. and EDC (1.1 eq.) was added portion-wise. After stirring for 1 hour at 0° C., the reaction mixture was allowed to warm to room temperature. The reaction was monitored by TLC and LC/MS. Usually after 12 hours stirring at RT, the reaction mixture was hydrolyzed, washed with sodium carbonate solution (10%), dried over MgSO4, and evaporated in vacuo to give a crude product. Flash chromatography on silica gel, eluting with 60% EtOAc in hexane gave, after evaporation, the expected product N-[2-(2-methylpiperidin-1-yl)ethyl]-4-(2-phenyl-4,5,6,7-tetrahydro-1H-indol-1-yl)benzamide (1) as a beige solid, in 80% yield (96% purity by HPLC). MS(ESI+): 442.7; MS(ESI−): 440.5. The reaction mixture was then cooled down to 0° C. After stirring for 1 hour at 0° C. to warm to room temperature Usually after 12 hours stirring at RT washed with sodium carbonate solution (10%) dried over MgSO4 evaporated in vacuo

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

Procedure: 15 mg (12%) of the target compound was obtained in the same manner of Example 1, using 3-(4-chloro-benzyl)-2,4-dioxoquinazoline-7-carboxylic acid (90 mg, 0.272 mol) obtained in Example 1 and 2-(2-methyl-piperidine-1-yl)-ethylamine (77 mL, 0.544 mmol).