(4-propan-2-yloxyphenyl)methanamine

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

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

Procedure: Sodium cyanoborohydride (330 mg) was added to a solution of 770 mg of p-isopropoxybenzaldehyde and 4.0 g of ammonium acetate in 20 ml of methanol, and the mixture was stirred at room temperature for 40 hours. The reaction mixture was adjusted to pH 2 or less by addition of concentrated hydrochloric acid, and then concentrated. The residue was dissolved in water and the solution was washed with ethyl acetate. The aqueous layer was adjusted to pH 11 or more by addition of solid potassium hydroxide, and the product was extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated aqueous solution of sodium chloride in that order, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 110 mg of p-isopropoxybenzylamine. concentrated The residue was dissolved in water the solution was washed with ethyl acetate The aqueous layer was adjusted to pH 11 or more by addition of solid potassium hydroxide the product was extracted with ethyl acetate The ethyl acetate layer was washed with water and saturated aqueous solution of sodium chloride in that order dried over anhydrous sodium sulfate concentrated under reduced pressure

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

Procedure: Sodium cyanoborohydride (330 mg) was added to a solution of 770 mg of p-isopropoxybenzaldehyde and 4.0 g of ammonium acetate in 20 ml of methanol, and the mixture was stirred at room temperature for 40 hours. The reaction mixture was adjusted to pH 2 or less by addition of concentrated hydrochloric acid, and then concentrated. The residue was dissolved in water and the solution was washed with ethyl acetate. The aqueous layer was adjusted to pH 11 or more by addition of solid potassium hydroxide, and the product was extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated aqueous solution of sodium chloride in that order, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 110 mg of p-isopropoxybenzylamine. concentrated The residue was dissolved in water the solution was washed with ethyl acetate The aqueous layer was adjusted to pH 11 or more by addition of solid potassium hydroxide the product was extracted with ethyl acetate The ethyl acetate layer was washed with water and saturated aqueous solution of sodium chloride in that order dried over anhydrous sodium sulfate concentrated under reduced pressure

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

Procedure: The title compound was prepared in 28% yield from 1-(4-isopropoxyphenyl)-methanamine and 3-fluoroisonicotinic acid according to the procedure for the preparation of Example 3. 1H NMR (400 MHz, DMSO-d6): δ 8.12 (s, 1H), 7.80 (d, 1H, J=5.0 Hz), 7.56 (d, 1H, J=5.0 Hz), 7.28 (d, 2H, J=8.0 Hz), 7.21 (d, 2H, J=8.0 Hz), 4.49 (s, 2H), 2.82-2.89 (m, 1H), 1.19 (d, 6H, J=4.5 Hz). [M+H] calc'd for C16H18N2O3, 287. found 287.

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

Procedure: The title compound was prepared in 28% yield from 1-(4-isopropoxyphenyl)-methanamine and 3-fluoroisonicotinic acid according to the procedure for the preparation of Example 3. 1H NMR (400 MHz, DMSO-d6): δ 8.12 (s, 1H), 7.80 (d, 1H, J=5.0 Hz), 7.56 (d, 1H, J=5.0 Hz), 7.28 (d, 2H, J=8.0 Hz), 7.21 (d, 2H, J=8.0 Hz), 4.49 (s, 2H), 2.82-2.89 (m, 1H), 1.19 (d, 6H, J=4.5 Hz). [M+H] calc'd for C16H18N2O3, 287. found 287.

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

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

Procedure: The title compound was prepared in 28% yield from 1-(4-isopropoxyphenyl)-methanamine and 3-fluoroisonicotinic acid according to the procedure for the preparation of Example 3. 1H NMR (400 MHz, DMSO-d6): δ 8.12 (s, 1H), 7.80 (d, 1H, J=5.0 Hz), 7.56 (d, 1H, J=5.0 Hz), 7.28 (d, 2H, J=8.0 Hz), 7.21 (d, 2H, J=8.0 Hz), 4.49 (s, 2H), 2.82-2.89 (m, 1H), 1.19 (d, 6H, J=4.5 Hz). [M+H] calc'd for C16H18N2O3, 287. Found 287.

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

Procedure: The title compound was prepared in 28% yield from 1-(4-isopropoxyphenyl)-methanamine and 3-fluoroisonicotinic acid according to the procedure for the preparation of Example 3. 1H NMR (400 MHz, DMSO-d6): δ 8.12 (s, 1H), 7.80 (d, 1H, J=5.0 Hz), 7.56 (d, 1H, J=5.0 Hz), 7.28 (d, 2H, J=8.0 Hz), 7.21 (d, 2H, J=8.0 Hz), 4.49 (s, 2H), 2.82-2.89 (m, 1H), 1.19 (d, 6H, J=4.5 Hz). [M+H] calc'd for C16H18N2O3, 287; found 287.

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

Procedure: Sodium cyanoborohydride (330 mg) was added to a solution of 770 mg of p-isopropoxybenzaldehyde and 4.0 g of ammonium acetate in 20 ml of methanol, and the mixture was stirred at room temperature for 40 hours. The reaction mixture was adjusted to pH 2 or less by addition of concentrated hydrochloric acid, and then concentrated. The residue was dissolved in water and the solution was washed with ethyl acetate. The aqueous layer was adjusted to pH 11 or more by addition of solid potassium hydroxide, and the product was extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated aqueous solution of sodium chloride in that order, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 110 mg of p-isopropoxybenzylamine. concentrated The residue was dissolved in water the solution was washed with ethyl acetate The aqueous layer was adjusted to pH 11 or more by addition of solid potassium hydroxide the product was extracted with ethyl acetate The ethyl acetate layer was washed with water and saturated aqueous solution of sodium chloride in that order dried over anhydrous sodium sulfate concentrated under reduced pressure

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

Procedure: The title compound was prepared in 28% yield from 1-(4-isopropoxyphenyl)-methanamine and 3-fluoroisonicotinic acid according to the procedure for the preparation of Example 3. 1H NMR (400 MHz, DMSO-d6): δ 8.12 (s, 1H), 7.80 (d, 1H, J=5.0 Hz), 7.56 (d, 1H, J=5.0 Hz), 7.28 (d, 2H, J=8.0 Hz), 7.21 (d, 2H, J=8.0 Hz), 4.49 (s, 2H), 2.82-2.89 (m, 1H), 1.19 (d, 6H, J=4.5 Hz). [M+H] calc'd for C16H18N2O3, 287. found 287.