1-cyclopentyl-N-[(1R)-1-phenylethyl]ethanimine

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

Procedure: (R)-1-Phenylethanamine (1.36 ml, 1.2 mmol) and triethylamine (7.46 ml, 53.5 mmol) were dissolved in DCM (30 ml) and cooled to 0° C. Titanium tetrachloride (0.49 ml, 4.46 mmol) was added, followed by the solution of 1-cyclopentyl-ethanone (1 g, 8.92 mmol) in DCM (5 ml). The reaction mixture was stirred 3 h at reflux temperature. After cooling to rt diethylether was added (130 ml) and the reaction mixture was filtered. The filtrate was collected and the solvents were evaporated at reduced pressure to give the product as yellow, viscous oil (2.04 g, crude quantitative). [1H-NMR (DMSO-d6, 600 MHz) δ 7.35 (d, 2H), 7.28 (t, 2H), 7.17 (t, 1H), 4.61 (q, 1H), 2.67-2.62 (m, 1H), 1.81 (s, 3H), 1.71-1.50 (m, 8H), 1.27 (d, 3H); LCMS RtL=2.706 min; [M+H]+=216.2] at reflux temperature was added (130 ml) the reaction mixture was filtered The filtrate was collected the solvents were evaporated at reduced pressure to give the product as yellow, viscous oil (2.04 g [1H-NMR (DMSO-d6, 600 MHz) δ 7.35 (d, 2H), 7.28 (t, 2H), 7.17 (t, 1H), 4.61 (q, 1H), 2.67-2.62 (m, 1H), 1.81 (s, 3H), 1.71-1.50 (m, 8H), 1.27 (d, 3H); LCMS RtL=2.706 min; [M+H]+=216.2]

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

Procedure: (R)-1-Phenylethanamine (1.36 ml, 1.2 mmol) and triethylamine (7.46 ml, 53.5 mmol) were dissolved in DCM (30 ml) and cooled to 0° C. Titanium tetrachloride (0.49 ml, 4.46 mmol) was added, followed by the solution of 1-cyclopentyl-ethanone (1 g, 8.92 mmol) in DCM (5 ml). The reaction mixture was stirred 3 h at reflux temperature. After cooling to rt diethylether was added (130 ml) and the reaction mixture was filtered. The filtrate was collected and the solvents were evaporated at reduced pressure to give the product as yellow, viscous oil (2.04 g, crude quantitative). [1H-NMR (DMSO-d6, 600 MHz) δ 7.35 (d, 2H), 7.28 (t, 2H), 7.17 (t, 1H), 4.61 (q, 1H), 2.67-2.62 (m, 1H), 1.81 (s, 3H), 1.71-1.50 (m, 8H), 1.27 (d, 3H); LCMS RtL=2.706 min; [M+H]+=216.2] at reflux temperature was added (130 ml) the reaction mixture was filtered The filtrate was collected the solvents were evaporated at reduced pressure to give the product as yellow, viscous oil (2.04 g [1H-NMR (DMSO-d6, 600 MHz) δ 7.35 (d, 2H), 7.28 (t, 2H), 7.17 (t, 1H), 4.61 (q, 1H), 2.67-2.62 (m, 1H), 1.81 (s, 3H), 1.71-1.50 (m, 8H), 1.27 (d, 3H); LCMS RtL=2.706 min; [M+H]+=216.2]

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

Procedure: (R)-1-Phenylethanamine (1.36 ml, 1.2 mmol) and triethylamine (7.46 ml, 53.5 mmol) were dissolved in DCM (30 ml) and cooled to 0° C. Titanium tetrachloride (0.49 ml, 4.46 mmol) was added, followed by the solution of 1-cyclopentyl-ethanone (1 g, 8.92 mmol) in DCM (5 ml). The reaction mixture was stirred 3 h at reflux temperature. After cooling to rt diethylether was added (130 ml) and the reaction mixture was filtered. The filtrate was collected and the solvents were evaporated at reduced pressure to give the product as yellow, viscous oil (2.04 g, crude quantitative). [1H-NMR (DMSO-d6, 600 MHz) δ 7.35 (d, 2H), 7.28 (t, 2H), 7.17 (t, 1H), 4.61 (q, 1H), 2.67-2.62 (m, 1H), 1.81 (s, 3H), 1.71-1.50 (m, 8H), 1.27 (d, 3H); LCMS RtL=2.706 min; [M+H]+=216.2] at reflux temperature was added (130 ml) the reaction mixture was filtered The filtrate was collected the solvents were evaporated at reduced pressure to give the product as yellow, viscous oil (2.04 g [1H-NMR (DMSO-d6, 600 MHz) δ 7.35 (d, 2H), 7.28 (t, 2H), 7.17 (t, 1H), 4.61 (q, 1H), 2.67-2.62 (m, 1H), 1.81 (s, 3H), 1.71-1.50 (m, 8H), 1.27 (d, 3H); LCMS RtL=2.706 min; [M+H]+=216.2]

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

Procedure: (R)-1-Phenylethanamine (1.36 ml, 1.2 mmol) and triethylamine (7.46 ml, 53.5 mmol) were dissolved in DCM (30 ml) and cooled to 0° C. Titanium tetrachloride (0.49 ml, 4.46 mmol) was added, followed by the solution of 1-cyclopentyl-ethanone (1 g, 8.92 mmol) in DCM (5 ml). The reaction mixture was stirred 3 h at reflux temperature. After cooling to rt diethylether was added (130 ml) and the reaction mixture was filtered. The filtrate was collected and the solvents were evaporated at reduced pressure to give the product as yellow, viscous oil (2.04 g, crude quantitative). [1H-NMR (DMSO-d6, 600 MHz) δ 7.35 (d, 2H), 7.28 (t, 2H), 7.17 (t, 1H), 4.61 (q, 1H), 2.67-2.62 (m, 1H), 1.81 (s, 3H), 1.71-1.50 (m, 8H), 1.27 (d, 3H); LCMS RtL=2.706 min; [M+H]+=216.2] at reflux temperature was added (130 ml) the reaction mixture was filtered The filtrate was collected the solvents were evaporated at reduced pressure to give the product as yellow, viscous oil (2.04 g [1H-NMR (DMSO-d6, 600 MHz) δ 7.35 (d, 2H), 7.28 (t, 2H), 7.17 (t, 1H), 4.61 (q, 1H), 2.67-2.62 (m, 1H), 1.81 (s, 3H), 1.71-1.50 (m, 8H), 1.27 (d, 3H); LCMS RtL=2.706 min; [M+H]+=216.2]