N-benzyl-N-methyl-1-phenylmethanamine

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of N-benzyl-(+)-methyl-benzylamine (8.5 mL, 40.4 mmol) in THF (100 mL) was cooled to 0° C., then n-butyl lithium (16 mL, [2.5 M], 40.4 mmol) was added and the resulting mixture stirred for 1 hour. The reaction mixture was cooled to −78° C., then a solution of 3-cyclohexyl-acrylic acid tert-butyl ester (7.71 g, 36.7 mmol) in THF (20 mL) was added dropwise for 30 min and the resulting mixture was stirred an additional 1 hour at −78° C. The reaction was quenched with NH4CT (s), and extracted with EtOAc, the organic layer was dried with MgSO4, filtered and evaporated under reduced pressure to yield a residue. The residue was purified by column chromatography (10%-70% EtOAc/heptane) to yield a residue. the resulting mixture was stirred an additional 1 hour at −78° C The reaction was quenched with NH4CT (s) extracted with EtOAc the organic layer was dried with MgSO4 filtered evaporated under reduced pressure to yield a residue The residue was purified by column chromatography (10%-70% EtOAc/heptane) to yield a residue

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of N-benzyl-(+)-methyl-benzylamine (8.5 mL, 40.4 mmol) in THF (100 mL) was cooled to 0° C., then n-butyl lithium (16 mL, [2.5 M], 40.4 mmol) was added and the resulting mixture stirred for 1 hour. The reaction mixture was cooled to −78° C., then a solution of 3-cyclohexyl-acrylic acid tert-butyl ester (7.71 g, 36.7 mmol) in THF (20 mL) was added dropwise for 30 min and the resulting mixture was stirred an additional 1 hour at −78° C. The reaction was quenched with NH4CT (s), and extracted with EtOAc, the organic layer was dried with MgSO4, filtered and evaporated under reduced pressure to yield a residue. The residue was purified by column chromatography (10%-70% EtOAc/heptane) to yield a residue. the resulting mixture was stirred an additional 1 hour at −78° C The reaction was quenched with NH4CT (s) extracted with EtOAc the organic layer was dried with MgSO4 filtered evaporated under reduced pressure to yield a residue The residue was purified by column chromatography (10%-70% EtOAc/heptane) to yield a residue

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

Procedure: In a similar manner to Example 1, 197.3 g (1.0 mol) of dibenzylamine and 165.1 g (1.6 mol) of formaldehyde (29.1%) are reacted in a 1 l autoclave; a maximum pressure of 1.8 MPa is established at a temperature of 160° C. After the end of the reaction, 30 g of hexene-1 are added and the organic phase is removed from the aqueous phase. The remaining organic phase is subsequently distilled. 191.8 g of N-methyldibenzylamine having a purity of 93.8% are isolated, corresponding to a yield of 85.1% of theory. is established at a temperature of 160° C are added the organic phase is removed from the aqueous phase The remaining organic phase is subsequently distilled

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of N-benzyl-(+)-methyl-benzylamine (8.5 mL, 40.4 mmol) in THF (100 mL) was cooled to 0° C., then n-butyl lithium (16 mL, [2.5 M], 40.4 mmol) was added and the resulting mixture stirred for 1 hour. The reaction mixture was cooled to −78° C., then a solution of 3-cyclohexyl-acrylic acid tert-butyl ester (7.71 g, 36.7 mmol) in THF (20 mL) was added dropwise for 30 min and the resulting mixture was stirred an additional 1 hour at −78° C. The reaction was quenched with NH4CT (s), and extracted with EtOAc, the organic layer was dried with MgSO4, filtered and evaporated under reduced pressure to yield a residue. The residue was purified by column chromatography (10%-70% EtOAc/heptane) to yield a residue. the resulting mixture was stirred an additional 1 hour at −78° C The reaction was quenched with NH4CT (s) extracted with EtOAc the organic layer was dried with MgSO4 filtered evaporated under reduced pressure to yield a residue The residue was purified by column chromatography (10%-70% EtOAc/heptane) to yield a residue