1-phenyl-N-prop-2-ynylmethanimine

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

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

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

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

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

Procedure: 10 g of ethyl magnesium bromide was added over 30 minutes to a stirred solution of 10.2 g of 1A in 100 ml of tetrahydrofuran at 0° C. The resulting mixture was stirred at that temperature for 30 minutes, then a solution of 7.75 g of trimethylsilyl chloride in 30 ml of tetrahydrofuran was added over 30 minutes. The mixture then was stirred at 0° C. for 90 minutes, treated with brine, dried (MgSO4) and the solvent was evaporated. The residue was distilled at 85°-90° C., 0.3 Torr., to give N-benzylidene-3-(trimethylsilyl)-2-propyn-1-amine (1B), as a water-white oil. The mixture then was stirred at 0° C. for 90 minutes dried (MgSO4) the solvent was evaporated The residue was distilled at 85°-90° C.

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

Procedure: 10 g of magnesium sulfate was added to a stirred solution of 13.8 g of propargylamine and 26.5 g of benzaldehyde in 75 ml of benzene and the resulting mixture was stirred at room temperature for 30 minutes. The mixture then was filtered and water was removed from the filtrate by azeotropic distillation. Then the remaining benzene was evaporated and the residue was distilled to give N-benzylidene-2-propyn-1-amine (1A) b.p.: 64°-66° C. (0.2 Torr.). The mixture then was filtered water was removed from the filtrate by azeotropic distillation Then the remaining benzene was evaporated the residue was distilled

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

Procedure: An aqueous 28% ammonia solution (166.4 g, 2.74 mol) and benzaldehyde (30.6 g, 0.288 mol) were mixed and a solution prepared by dissolving propargyl methanesulfonate (36.7 g, 0.274 mol) in 147 g of toluene was added dropwise at 20°-25° C. over 3 hours to the solution, followed by stirring at the same temperature for 3 hours. After separating, the organic phase and aqueous phase were obtained. The organic phase obtained by washing the aqueous phase twice with 25 g of toluene was combined with the above organic phase and concentrated until the weight became 78 g to obtain a toluene solution of N-benzylidene-2-propynylamine. a solution prepared was added dropwise at 20°-25° C. over 3 hours to the solution After separating the organic phase and aqueous phase were obtained The organic phase obtained by washing the aqueous phase twice with 25 g of toluene concentrated until the weight

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

Procedure: Propargyl methanesulfonate (31.6 g, 0.236 mol) and benzaldehyde (31.9 g, 0.3 mol) were dissolved in 103 g of toluene and an aqueous 28% ammonia solution (122 g, 2 mol) was added dropwise at 21° C. over 8 hours to the solution, followed by stirring at the same temperature for 15 hours. After separating, the resultant organic phase was washed with water and concentrated until the weight became 57.3 g to obtain a toluene solution containing 28.6 g (yield: 85%) of N-benzylidene-2-propynylamine. After separating the resultant organic phase was washed with water concentrated until the weight to obtain a toluene solution

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

Procedure: Propargyl methanesulfonate (46.8 g, 0.35 mol) and benzaldehyde (47.0 g, 0.44 mol) were dissolved in 148 g of toluene and an aqueous 28% ammonia solution (180 g, 2.96 mol) was added dropwise at 24° C. over 7.5 hours to the solution, followed by stirring at the same temperature for 15 hours. After separating, the resultant organic phase was washed with water and concentrated to obtain 56.5 g of a crude product containing 40.0 g (yield: 80%) of N-benzylidene-2-propynylamine. The resulting crude product was distilled to obtain 34.9 g (purity: 97%, boiling point: 80°-83° C./2.5 mmHg) of N-benzylidene-2-propylamine. After separating the resultant organic phase was washed with water concentrated to obtain 56.5 g of a crude product