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With water; triphenylphosphine In tetrahydrofuran at 20℃; for 22 h;
INTERMEDIATE 9 - PREPARATION OF 3-(5-Chloro-1 H-indol-3-yl)propan-1-amine. To a solution of 3-(3-Azidopropyl)-5-chloro-1 H-indole (0.299 g; 1.27 mmol) in THF (9 mL) were added triphenylphosphine (0.354 g; 1.34 mmol) and water (0.6 mL). The reaction mixture was stirred at room temperature for 22 hours and was then concentrated under reduced pressure. The residue was dissolved in dichloromethane (10 mL) and 10 mL of 6N hydrochloric acid were added. After separation, the aqueous layer was further extracted with dichloromethane (2x10 mL) and the pH was adjusted to 14 with an aqueous solution of sodium hydroxide 6N. This basic solution was extracted dichloromethane (3x20 mL) and the combined organic layer was dried over magnesium sulphate, and evaporated to afford 0.089 g (34percent) of 3-(5-Chloro-1 H-indol-3-yl)propan-1 -amine as a white solid.ESI/APCI(+): 209 (M+H); ESI/APCI(-): 207 (M-H).
34%
With water; triphenylphosphine In tetrahydrofuran at 20℃; for 22 h;
INTERMEDIATE 23 - PREPARATION OF 3-(5-Chloro-1 H-indol-3-yl)propan-1-amine. To a solution of 3-(3-azidopropyl)-5-chloro-1 H-indole (0.299 g; 1.27 mmol) in tetrahydrofuran (9 mL) were added triphenylphosphine (0.354 g; 1.34 mmol) and water (0.6 mL). The reaction mixture was stirred at room temperature for 22 hours and was then evaporated to dryness. The residue was dissolved in dichloromethane (10 mL) and 10 mL of 6N hydrochloric acid were added. After separation, the aqueous layer was further extracted with dichloromethane (2x10 mL) and the pH was adjusted to 14 with a solution of sodium hydroxide 6N. This basic solution was extracted with dichloromethane (3x20 mL) and the combined organic layer was dried over magnesium sulfate, and evaporated to afford 0.089 g (34percent) of 3-(5-chloro-1/-/-indol-3-yl)propan-1 -amine as a white solid.ESI/APCI(+): 209 (M+H); ESI/APCI(-): 207 (M-H).
34%
With water; triphenylphosphine In tetrahydrofuran at 20℃; for 22 h;
To a solution of 3-(3-Azidopropyl)-5-chloro-1H-indole (0.299 g; 1.27 mmol) in THF (9 mL) were added triphenylphosphine (0.354 g; 1.34 mmol) and water (0.6 mL). The reaction mixture was stirred at room temperature for 22 hours and was then concentrated under reduced pressure. The residue was dissolved in dichloromethane (10 mL) and 10 mL of 6N hydrochloric acid were added. After separation, the aqueous layer was further extracted with dichloromethane (2×10 mL) and the pH was adjusted to 14 with an aqueous solution of sodium hydroxide 6N. This basic solution was extracted dichloromethane (3×20 mL) and the combined organic layer was dried over magnesium sulphate, and evaporated to afford 0.089 g (34percent) of 3-(5-Chloro-1H-indol-3-yl)propan-1-amine as a white solid. [0531] ESI/APCI(+): 209 (M+H); ESI/APCI(−): 207 (M−H).
34%
With water; triphenylphosphine In tetrahydrofuran at 20℃; for 22 h;
INTERMEDIATE 40 - PREPARATION OF 3-(5-Chloro-1 A7-indol-3-yl)propan-1 -amine.; To a solution of intermediate 39 (0.299 g; 1.27 mmol) in tetrahydrofuran (9 mL) were added triphenylphosphine (0.354 g; 1.34 mmol) and water (0.6 mL). The reaction mixture was stirred at room temperature for 22 h and was then evaporated to dryness. The residue was dissolved in dichloromethane (10 mL) and 10 mL of 6N hydrochloric acid were added. After separation, the aqueous layer was further extracted with dichloromethane (2x10 mL) and the pH was adjusted to 14 with a solution of sodium hydroxide 6N. This basic solution was extracted dichloromethane (3x20 mL) and the combined organic layer was dried over magnesium sulfate, and evaporated to afford 0.089 g (34percent) of 3-(5-chloro-1H-indol-3-yl)propan-1 -amine as a white solid. ESI/APCI(+): 209 (M+H). ESI/APCK-): 207 (M -H).
0.089 g
With water; triphenylphosphine In tetrahydrofuran at 20℃; for 22 h;
To a solution of 3-(3-azidopropyl)-5-chloro-1H-indole (0.299 g; 1.27 mmol) in tetrahydrofuran (9 mL) were added triphenylphosphine (0.354 g; 1.34 mmol) and water (0.6 mL). The reaction mixture was stirred at room temperature for 22 hours and was then evaporated to dryness. The residue was dissolved in dichloromethane (10 mL) and 10 mL of 6N hydrochloric acid were added. After separation, the aqueous layer was further extracted with dichloromethane (2×10 mL) and the pH was adjusted to 14 with a solution of sodium hydroxide 6N. This basic solution was extracted with dichloromethane (3×20 mL) and the combined organic layer was dried over magnesium sulfate, and evaporated to afford 0.089 g (34percent) of 3-(5-chloro-1H-indol-3-yl)propan-1-amine as a white solid. [0600] ESI/APCI(+): 209 (M+H); ESI/APCI(−): 207 (M−H).
With water; triphenylphosphine; In tetrahydrofuran; at 20℃; for 22h;
INTERMEDIATE 9 - PREPARATION OF 3-(5-Chloro-1 H-indol-3-yl)propan-1-amine. To a solution of 3-(3-Azidopropyl)-5-chloro-1 H-indole (0.299 g; 1.27 mmol) in THF (9 mL) were added triphenylphosphine (0.354 g; 1.34 mmol) and water (0.6 mL). The reaction mixture was stirred at room temperature for 22 hours and was then concentrated under reduced pressure. The residue was dissolved in dichloromethane (10 mL) and 10 mL of 6N hydrochloric acid were added. After separation, the aqueous layer was further extracted with dichloromethane (2x10 mL) and the pH was adjusted to 14 with an aqueous solution of sodium hydroxide 6N. This basic solution was extracted dichloromethane (3x20 mL) and the combined organic layer was dried over magnesium sulphate, and evaporated to afford 0.089 g (34%) of 3-(5-Chloro-1 H-indol-3-yl)propan-1 -amine as a white solid.ESI/APCI(+): 209 (M+H); ESI/APCI(-): 207 (M-H).
34%
With water; triphenylphosphine; In tetrahydrofuran; at 20℃; for 22h;
INTERMEDIATE 23 - PREPARATION OF 3-(5-Chloro-1 H-indol-3-yl)propan-1-amine. To a solution of 3-(3-azidopropyl)-5-chloro-1 H-indole (0.299 g; 1.27 mmol) in tetrahydrofuran (9 mL) were added triphenylphosphine (0.354 g; 1.34 mmol) and water (0.6 mL). The reaction mixture was stirred at room temperature for 22 hours and was then evaporated to dryness. The residue was dissolved in dichloromethane (10 mL) and 10 mL of 6N hydrochloric acid were added. After separation, the aqueous layer was further extracted with dichloromethane (2x10 mL) and the pH was adjusted to 14 with a solution of sodium hydroxide 6N. This basic solution was extracted with dichloromethane (3x20 mL) and the combined organic layer was dried over magnesium sulfate, and evaporated to afford 0.089 g (34%) of 3-(5-chloro-1/-/-indol-3-yl)propan-1 -amine as a white solid.ESI/APCI(+): 209 (M+H); ESI/APCI(-): 207 (M-H).
34%
With water; triphenylphosphine; In tetrahydrofuran; at 20℃; for 22h;
To a solution of 3-(3-Azidopropyl)-5-chloro-1H-indole (0.299 g; 1.27 mmol) in THF (9 mL) were added triphenylphosphine (0.354 g; 1.34 mmol) and water (0.6 mL). The reaction mixture was stirred at room temperature for 22 hours and was then concentrated under reduced pressure. The residue was dissolved in dichloromethane (10 mL) and 10 mL of 6N hydrochloric acid were added. After separation, the aqueous layer was further extracted with dichloromethane (2×10 mL) and the pH was adjusted to 14 with an aqueous solution of sodium hydroxide 6N. This basic solution was extracted dichloromethane (3×20 mL) and the combined organic layer was dried over magnesium sulphate, and evaporated to afford 0.089 g (34%) of 3-(5-Chloro-1H-indol-3-yl)propan-1-amine as a white solid. [0531] ESI/APCI(+): 209 (M+H); ESI/APCI(-): 207 (M-H).
34%
With water; triphenylphosphine; In tetrahydrofuran; at 20℃; for 22h;
INTERMEDIATE 40 - PREPARATION OF 3-(5-Chloro-1 A7-indol-3-yl)propan-1 -amine.; To a solution of intermediate 39 (0.299 g; 1.27 mmol) in tetrahydrofuran (9 mL) were added triphenylphosphine (0.354 g; 1.34 mmol) and water (0.6 mL). The reaction mixture was stirred at room temperature for 22 h and was then evaporated to dryness. The residue was dissolved in dichloromethane (10 mL) and 10 mL of 6N hydrochloric acid were added. After separation, the aqueous layer was further extracted with dichloromethane (2x10 mL) and the pH was adjusted to 14 with a solution of sodium hydroxide 6N. This basic solution was extracted dichloromethane (3x20 mL) and the combined organic layer was dried over magnesium sulfate, and evaporated to afford 0.089 g (34%) of 3-(5-chloro-1H-indol-3-yl)propan-1 -amine as a white solid. ESI/APCI(+): 209 (M+H). ESI/APCK-): 207 (M -H).
0.089 g
With water; triphenylphosphine; In tetrahydrofuran; at 20℃; for 22h;
To a solution of 3-(3-azidopropyl)-5-chloro-1H-indole (0.299 g; 1.27 mmol) in tetrahydrofuran (9 mL) were added triphenylphosphine (0.354 g; 1.34 mmol) and water (0.6 mL). The reaction mixture was stirred at room temperature for 22 hours and was then evaporated to dryness. The residue was dissolved in dichloromethane (10 mL) and 10 mL of 6N hydrochloric acid were added. After separation, the aqueous layer was further extracted with dichloromethane (2×10 mL) and the pH was adjusted to 14 with a solution of sodium hydroxide 6N. This basic solution was extracted with dichloromethane (3×20 mL) and the combined organic layer was dried over magnesium sulfate, and evaporated to afford 0.089 g (34%) of 3-(5-chloro-1H-indol-3-yl)propan-1-amine as a white solid. [0600] ESI/APCI(+): 209 (M+H); ESI/APCI(-): 207 (M-H).
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