2-(4-methylphenyl)ethanamine

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:

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:

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 12.0 g (89 mmol) of 2-p-tolylethylamine and 11.21 ml (111 mmol) of benzaldehyde in PPA (300 g) was heated at 100° C. for 5 days. After cooling to RT it was poured into a saturated aqueous K2CO3 solution (1200 ml). Following the addition of DCM (300 ml) it was stirred for 50 min at RT. Then the phases were separated and the aqueous phase was extracted with DCM (2×500 ml). The organic phases were combined, dried over Na2SO4, filtered and concentrated to small volume under vacuum. 16.3 g of 7-methyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline were obtained as the crude product, which was reacted further with no additional purification. After cooling to RT it Then the phases were separated the aqueous phase was extracted with DCM (2×500 ml) dried over Na2SO4 filtered concentrated to small volume under vacuum

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

Procedure: Methyl N-cyano-2-pyridinecarboximidate (0.50 g, 3.1 mmol) was dissolved in methanol (10 ml), 2-(p-tolyl)ethylamine (0.47 g, 3.5 mmol) was added, and the resulting mixture was stirred at room temperature for 1 hour. After the reaction was completed, the reaction solution was concentrated under reduced pressure, and the residue thus obtained was crystallized from methanol-diethyl ether to give the title compound (0.76 g, 2.9 mmol, yield: 93%) as colorless crystals. the reaction solution was concentrated under reduced pressure the residue thus obtained was crystallized from methanol-diethyl ether