[4-(methylaminomethyl)phenyl]methanamine

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

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

Conditions: temp:23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Lithium aluminum hydride (1.8 g, 44.5 mmol, 3.5 equiv) was added portionwise to a solution of N-mono(Boc)-p-xylylenediamine in tetrahydrofuran (100 mL) at 0° C. Gas evolution was observed. The grey suspension was stirred at 23° C. for 2 h, by which time gas evolution had ceased. The reaction mixture was refluxed for 16 h, then carefully quenched at 0° C. by the dropwise addition of water (1.8 mL). Gas evolution was seen. 15% Aqueous sodium hydroxide (1.8 mL) and water (5.4 mL) was added dropwise to the suspension at 23° C. The mixture was stirred at 23° C. for 0.5 h, then filtered. The filter cake was washed with tetrahydrofuran and dichloromethane. The filtrate was concentrated, providing crude N-mono(methyl)-p-xylylenediamine (0.68 g) as a yellow oil. The reaction mixture was refluxed for 16 h carefully quenched at 0° C. by the dropwise addition of water (1.8 mL) 15% Aqueous sodium hydroxide (1.8 mL) and water (5.4 mL) was added dropwise to the suspension at 23° C The mixture was stirred at 23° C. for 0.5 h filtered The filter cake was washed with tetrahydrofuran and dichloromethane The filtrate was concentrated