1-phenyl-N-propan-2-ylmethanimine

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

Procedure: To a three neck round bottom flask, equipped with a cold water condenser, 30 g of water and 26.5 g of benzaldehyde were added. The mixture was mixed using a magnetic stirrer for 3 minutes at room temperature. i-Propylamine (17.7 g) was added to the reaction flask in one portion, followed by vigorous stirring for 40 minutes. The agitation was stopped and the reaction mixture was allowed to stand for at least 15 minutes. The lower aqueous layer was separated from the reaction mixture. The upper layer was collected and dried over magnesium sulfate to give 38.9 g of product. This crude product could be further purified by distillation, collecting the fraction between 94°-95° C./18 mmHg. 1H NMR (300 Hz, CDCl3, ppm): 8.29 (1H, s), 7.70 (2H, m), 7.38 (3H, m), 3.53 (hep. J=6.3 Hz), 1.27 (9H, d, J=6.3 Hz); IR (NaCl film, cm-1): 3061, 3026, 2930, 2835, 1647, 1581, 1450, 1382, 1306, 1141,967, 755, 693. To a three neck round bottom flask, equipped with a cold water condenser The mixture was mixed for 3 minutes at room temperature to stand for at least 15 minutes The lower aqueous layer was separated from the reaction mixture The upper layer was collected dried over magnesium sulfate

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

Procedure: To a three neck round bottom flask, equipped with a cold water condenser, 30 g of water and 26.5 g of benzaldehyde were added. The mixture was mixed using a magnetic stirrer for 3 minutes at room temperature. i-Propylamine (17.7 g) was added to the reaction flask in one portion, followed by vigorous stirring for 40 minutes. The agitation was stopped and the reaction mixture was allowed to stand for at least 15 minutes. The lower aqueous layer was separated from the reaction mixture. The upper layer was collected and dried over magnesium sulfate to give 38.9 g of product. This crude product could be further purified by distillation, collecting the fraction between 94°-95° C./18 mmHg. 1H NMR (300 Hz, CDCl3, ppm): 8.29 (1H, s), 7.70 (2H, m), 7.38 (3H, m), 3.53 (hep. J=6.3 Hz), 1.27 (9H, d, J=6.3 Hz); IR (NaCl film, cm-1): 3061, 3026, 2930, 2835, 1647, 1581, 1450, 1382, 1306, 1141,967, 755, 693. To a three neck round bottom flask, equipped with a cold water condenser The mixture was mixed for 3 minutes at room temperature to stand for at least 15 minutes The lower aqueous layer was separated from the reaction mixture The upper layer was collected dried over magnesium sulfate

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-benzylideneisopropylamine (7.5 g, 51 mmol) in benzene (10 mL) at 0° C. under a nitrogen blanket was added a solution of indole (5.0 g, 43 mmol) AcOH (30 mL) over a 3-hour period, after which the stirring was continued at 0° C. for an additional 3 hours. The bulk of the solvent was removed under reduced pressure and the remaining reaction mixture was poured into 400 mL of ice water. The mixture was extracted with Et2O (3×75 mL), and the aqueous layer was cooled to 0° C. and made basic with 30% aqueous NaOH to a pH 11–12 range. The precipitate was extracted with CH2Cl2 (2×75 mL) and the combined organic extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure to provide gramine Intermediate 6 as a yellow semisolid (3.06 g, 27%): TLC Rf (1:1 CH2Cl2/EtOAC)=0.45. The bulk of the solvent was removed under reduced pressure the remaining reaction mixture The mixture was extracted with Et2O (3×75 mL) The precipitate was extracted with CH2Cl2 (2×75 mL) the combined organic extracts were dried over Na2SO4 filtered the solvent was removed under reduced pressure

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-benzylideneisopropylamine (7.5 g, 51 mmol) in benzene (10 mL) at 0° C. under a nitrogen blanket was added a solution of indole (5.0 g, 43 mmol) AcOH (30 mL) over a 3-hour period, after which the stirring was continued at 0° C. for an additional 3 hours. The bulk of the solvent was removed under reduced pressure and the remaining reaction mixture was poured into 400 mL of ice water. The mixture was extracted with Et2O (3×75 mL), and the aqueous layer was cooled to 0° C. and made basic with 30% aqueous NaOH to a pH 11–12 range. The precipitate was extracted with CH2Cl2 (2×75 mL) and the combined organic extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure to provide gramine Intermediate 6 as a yellow semisolid (3.06 g, 27%): TLC Rf (1:1 CH2Cl2/EtOAC)=0.45. The bulk of the solvent was removed under reduced pressure the remaining reaction mixture The mixture was extracted with Et2O (3×75 mL) The precipitate was extracted with CH2Cl2 (2×75 mL) the combined organic extracts were dried over Na2SO4 filtered the solvent was removed under reduced pressure

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-benzylideneisopropylamine (7.5 g, 51 mmol) in benzene (10 mL) at 0° C. under a nitrogen blanket was added a solution of indole (5.0 g, 43 mmol) AcOH (30 mL) over a 3-hour period, after which the stirring was continued at 0° C. for an additional 3 hours. The bulk of the solvent was removed under reduced pressure and the remaining reaction mixture was poured into 400 mL of ice water. The mixture was extracted with Et2O (3×75 mL), and the aqueous layer was cooled to 0° C. and made basic with 30% aqueous NaOH to a pH 11–12 range. The precipitate was extracted with CH2Cl2 (2×75 mL) and the combined organic extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure to provide gramine Intermediate 6 as a yellow semisolid (3.06 g, 27%): TLC Rf (1:1 CH2Cl2/EtOAC)=0.45. The bulk of the solvent was removed under reduced pressure the remaining reaction mixture The mixture was extracted with Et2O (3×75 mL) The precipitate was extracted with CH2Cl2 (2×75 mL) the combined organic extracts were dried over Na2SO4 filtered the solvent was removed under reduced pressure