3-(methylaminomethyl)phenol

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: The 3-hydroxybenzylamine derivatives used in Examples 26 to 48, such as (E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-ethyl-3-hydroxybenzylamine, (E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-propyl-3-hydroxybenzylamine or (E)-N-ethyl-N-(6-methoxy-6-methyl-2-hepten-4-ynyl)-3-hydroxybenzylamine, were obtained by performing the same reaction as in Referential Example 26 except that in place of the starting methylamine-methanol solution, a methanol solution of ethylamine or propylamine was used and as required, 1-bromo-6-methoxy-6-methyl-2-hepten-4-yne was used instead of 1-bromo-6,6-dimethyl-2-hepten-4-yne was used. were obtained

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

Procedure: 10.0 g of 3-hydroxybenzaldehyde and 9.55 g of a 40% methanol solution of methylamine were mixed, and then the solvent was evaporated. The resulting Schiff base was dissolved in 50 ml of ethanol, and with stirring under ice cooling, 10.0 g of sodium borohydride was added. The mixture was stirred overnight at room temperature. The solvent was evaporated under reduced pressure, and ethyl acetate and a saturated aqueous solution of sodium chloride were added to extract it. The organic layer was separated, and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography Wakogel C-100, 100 g; eluting solvent: methylene chloride/methanol=10/1→5/1) to give 8.88 g (yield Λ%) of N-methyl-3-hydroxybenzylamine as pale yellow crystals, m.p. 138°-140° C. the solvent was evaporated The resulting Schiff base was dissolved in 50 ml of ethanol 10.0 g of sodium borohydride was added The mixture was stirred overnight at room temperature The solvent was evaporated under reduced pressure, and ethyl acetate a saturated aqueous solution of sodium chloride were added to extract it The organic layer was separated dried over anhydrous sodium sulfate The solvent was evaporated the residue was purified by silica gel column chromatography Wakogel C-100, 100 g

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

Procedure: 10.0 g of 3-hydroxybenzaldehyde and 9.55 g of a 40% methanol solution of methylamine were mixed, and then the solvent was evaporated. The resulting Schiff base was dissolved in 50 ml of ethanol, and with stirring under ice cooling, 10.0 g of sodium borohydride was added The mixture was stirred overnight at room temperature. The solvent was evaporated under reduced pressure, and the residue was extracted with ethyl acetate and a saturated aqueous sodium chloride solution. The organic layer was separated, and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography [Wakogel C-100, 100 g; eluting solvent: methylene chloride/methanol=10/1→5/1to give 8.88 g (yield 79%) of N-methyl-3-hydroxybenzylamine as pale yellow crystals having a melting point of 138° to 140° C. the solvent was evaporated The resulting Schiff base was dissolved in 50 ml of ethanol 10.0 g of sodium borohydride was added The mixture was stirred overnight at room temperature The solvent was evaporated under reduced pressure the residue was extracted with ethyl acetate The organic layer was separated dried over anhydrous sodium sulfate The solvent was evaporated the residue was purified by silica gel column chromatography [Wakogel C-100, 100 g

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

Procedure: 10.0 g of 3-hydroxybenzaldehyde and 9.55 g of a 40% methanol solution of methylamine were mixed, and then the solvent was evaporated. The resulting Schiff base was dissolved in 50 ml of ethanol, and with stirring under ice cooling, 10.0 g of sodium borohydride was added The mixture was stirred overnight at room temperature. The solvent was evaporated under reduced pressure, and the residue was extracted with ethyl acetate and a saturated aqueous sodium chloride solution. The organic layer was separated, and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography [Wakogel C-100, 100 g; eluting solvent: methylene chloride/methanol=10/1→5/1to give 8.88 g (yield 79%) of N-methyl-3-hydroxybenzylamine as pale yellow crystals having a melting point of 138° to 140° C. the solvent was evaporated The resulting Schiff base was dissolved in 50 ml of ethanol 10.0 g of sodium borohydride was added The mixture was stirred overnight at room temperature The solvent was evaporated under reduced pressure the residue was extracted with ethyl acetate The organic layer was separated dried over anhydrous sodium sulfate The solvent was evaporated the residue was purified by silica gel column chromatography [Wakogel C-100, 100 g

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

Procedure: 10.0 g of 3-hydroxybenzaldehyde and 9.55 g of a 40% methanol solution of methylamine were mixed, and then the solvent was evaporated. The resulting Schiff base was dissolved in 50 ml of ethanol, and with stirring under ice cooling, 10.0 g of sodium borohydride was added The mixture was stirred overnight at room temperature. The solvent was evaporated under reduced pressure, and the residue was extracted with ethyl acetate and a saturated aqueous sodium chloride solution. The organic layer was separated, and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography [Wakogel C-100, 100 g; eluting solvent: methylene chloride/methanol=10/1→5/1to give 8.88 g (yield 79%) of N-methyl-3-hydroxybenzylamine as pale yellow crystals having a melting point of 138° to 140° C. the solvent was evaporated The resulting Schiff base was dissolved in 50 ml of ethanol 10.0 g of sodium borohydride was added The mixture was stirred overnight at room temperature The solvent was evaporated under reduced pressure the residue was extracted with ethyl acetate The organic layer was separated dried over anhydrous sodium sulfate The solvent was evaporated the residue was purified by silica gel column chromatography [Wakogel C-100, 100 g