3-(4-methylphenyl)propan-1-amine

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

Procedure: 2-(4-Methylphenyl)propionamide (4 g) in dry tetrahydrofuran was added dropwise under nitrogen to lithium alumimium hydride (0.93 g) in dry tetrahydrofuran. The mixture was refluxed for 1 h at the end of addition. Water (1 ml), 2N. NaOH (1 ml), further water (3 ml) were added, the mixture filtered and the filtrate evaporated to give 3-(4-methylphenyl)propanamine (3.5 g). The mixture was refluxed for 1 h at the end of addition the mixture filtered the filtrate evaporated

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

Procedure: 2-(4-Methylphenyl)propionamide (4 g) in dry tetrahydrofuran was added dropwise under nitrogen to lithium alumimium hydride (0.93 g) in dry tetrahydrofuran. The mixture was refluxed for 1 h at the end of addition. Water (1 ml), 2N. NaOH (1 ml), further water (3 ml) were added, the mixture filtered and the filtrate evaporated to give 3-(4-methylphenyl)propanamine (3.5 g). The mixture was refluxed for 1 h at the end of addition the mixture filtered the filtrate evaporated

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

Procedure: The title compound was prepared in the manner described in Example 9 using phenylglyoxal and 3-(4-Methylphenyl)propanamine. Recrystallization of the chromatographed material from benzene-hexane gave the title compound m.p. 114-116. τ(CDCL3) 8.15 (2H, m), 7.7 (3H, s), 6.9-7.5 (6H, m+2H, disappears with D2O), 5.3 (1H, m), 2.9 (4H, s), 2.7 (5H, m). The title compound was prepared in the manner Recrystallization of the chromatographed material from benzene-hexane

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

Procedure: The title compound was prepared in the manner described in Example 9 using phenylglyoxal and 3-(4-Methylphenyl)propanamine. Recrystallization of the chromatographed material from benzene-hexane gave the title compound m.p. 114-116. τ(CDCL3) 8.15 (2H, m), 7.7 (3H, s), 6.9-7.5 (6H, m+2H, disappears with D2O), 5.3 (1H, m), 2.9 (4H, s), 2.7 (5H, m). The title compound was prepared in the manner Recrystallization of the chromatographed material from benzene-hexane

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

Procedure: The title compound was prepared in the manner described in Example 9 using 3-trifluoromethylphenylglyoxal and 3-(4-methylphenyl)propanamine. Recrystallization of the chromatographed material from hexane gave the title compound m.p. 96-98. τ(CDCl3) 8.0-8.5 (2H, m), 7.7 (3H, s), 7.0-7.5 (6H, m+2H, disappears with D2O), 5.3 (1H, dd), 2.9 (4H, s), 2.3-2.7 (4H, m). The title compound was prepared in the manner Recrystallization of the chromatographed material from hexane

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

Procedure: The title compound was prepared in the manner described in Example 9 using 3-trifluoromethylphenylglyoxal and 3-(4-methylphenyl)propanamine. Recrystallization of the chromatographed material from hexane gave the title compound m.p. 96-98. τ(CDCl3) 8.0-8.5 (2H, m), 7.7 (3H, s), 7.0-7.5 (6H, m+2H, disappears with D2O), 5.3 (1H, dd), 2.9 (4H, s), 2.3-2.7 (4H, m). The title compound was prepared in the manner Recrystallization of the chromatographed material from hexane

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

Procedure: The title compound was prepared in the manner described in Example 9 using 3-chlorophenylglyoxal and 3-(4-methylphenyl)propanamine. Recrystallisation of the chromatographed material from ether gave the title compound, mp 115°-117.5°. The title compound was prepared in the manner Recrystallisation of the chromatographed material from ether

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

Procedure: The title compound was prepared in the manner described in Example 9 using 3-chlorophenylglyoxal and 3-(4-methylphenyl)propanamine. Recrystallisation of the chromatographed material from ether gave the title compound, mp 115°-117.5°. The title compound was prepared in the manner Recrystallisation of the chromatographed material from ether

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

Procedure: 2-(4-Methylphenyl)propionamide (4 g) in dry tetrahydrofuran was added dropwise under nitrogen to lithium alumimium hydride (0.93 g) in dry tetrahydrofuran. The mixture was refluxed for 1 h at the end of addition. Water (1 ml), 2N. NaOH (1 ml), further water (3 ml) were added, the mixture filtered and the filtrate evaporated to give 3-(4-methylphenyl)propanamine (3.5 g). The mixture was refluxed for 1 h at the end of addition the mixture filtered the filtrate evaporated

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

Procedure: The title compound was prepared in the manner described in Example 9 using phenylglyoxal and 3-(4-Methylphenyl)propanamine. Recrystallization of the chromatographed material from benzene-hexane gave the title compound m.p. 114-116. τ(CDCL3) 8.15 (2H, m), 7.7 (3H, s), 6.9-7.5 (6H, m+2H, disappears with D2O), 5.3 (1H, m), 2.9 (4H, s), 2.7 (5H, m). The title compound was prepared in the manner Recrystallization of the chromatographed material from benzene-hexane

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

Procedure: The title compound was prepared in the manner described in Example 9 using 3-trifluoromethylphenylglyoxal and 3-(4-methylphenyl)propanamine. Recrystallization of the chromatographed material from hexane gave the title compound m.p. 96-98. τ(CDCl3) 8.0-8.5 (2H, m), 7.7 (3H, s), 7.0-7.5 (6H, m+2H, disappears with D2O), 5.3 (1H, dd), 2.9 (4H, s), 2.3-2.7 (4H, m). The title compound was prepared in the manner Recrystallization of the chromatographed material from hexane

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

Procedure: The title compound was prepared in the manner described in Example 9 using 3-chlorophenylglyoxal and 3-(4-methylphenyl)propanamine. Recrystallisation of the chromatographed material from ether gave the title compound, mp 115°-117.5°. The title compound was prepared in the manner Recrystallisation of the chromatographed material from ether