(Z)-3-phenylprop-2-en-1-amine

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

Procedure: 12.34 g (0.048 mol) of 2,4-dichlorophenacylimidazole and 6.66 g (0.05 mol) of cinnamylamine were suspended in 100 ml of toluene and the suspension was heated under reflux, using a water separator, until no further water of reaction was separated off. The solvent was removed in vacuo, after which 17.4 g (98% of theory) of a viscous oil were obtained. the suspension was heated under reflux was separated off The solvent was removed in vacuo after which 17.4 g (98% of theory) of a viscous oil were obtained

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

Procedure: (E)-N-Cinnamyl-2-naphthalenecarboxamide may be obtained in the following manner: working in a manner similar to that described in Example 21 for the preparation of (E)-3-chloro-N-cinnamylbenzamide, starting with cinnamylamine (5.3 g) and 2-naphthoic acid (7.6 g), and after recrystallization in ethyl acetate, (E)-N-cinnamyl-2-naphthalenecarboxamide (4.3 g) is obtained. after recrystallization in ethyl acetate

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

Procedure: 120 mg (0.450 mmol) of 4-(3-chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid and 71.9 mg (0.540 mmol) of 3-phenyl-2-propene-1-ylamine were dissolved in 10 ml of DMF. 129 mg (0.675 mmol) of WSC hydrochloride was added to the obtained solution under cooling with ice, and they were stirred at room temperature overnight. After the concentration under reduced pressure, the reaction mixture was diluted with ethyl acetate and then washed with 1 N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (dichloromethane/methanol=50/1 to 10/1) to obtain the title compound. under cooling with ice, and they After the concentration under reduced pressure the reaction mixture was diluted with ethyl acetate washed with 1 N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution The organic layer was dried over anhydrous magnesium sulfate concentrated under reduced pressure The residue was purified by the silica gel chromatography (dichloromethane/methanol=50/1 to 10/1)

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

Procedure: 110 mg (0.243 mmol) of 4-(3-chlorophenyl)-6-[(2-cyclohexylethoxy)methyl]-2-phenyl-1,4-dihydropyrimidine-5-carboxylic acid and 38.8 mg (0.292 mmol) of cinnamylamine were dissolved in 10 ml of dichloromethane. 69.9 mg (0.365 mmol) of WSC hydrochloride and 37.2 mg (0.243 mmol) of HOBT were added to the obtained solution under cooling with ice, and they were stirred at room temperature for 3 hours. The reaction mixture was diluted with dichloromethane and then washed with saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1 to 1/1) to obtain the title compound. under cooling with ice, and they washed with saturated aqueous sodium hydrogencarbonate solution The organic layer was dried over anhydrous sodium sulfate concentrated under reduced pressure The residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1 to 1/1)

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

Procedure: 120 mg (0.450 mmol) of 4-(3-chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid and 71.9 mg (0.540 mmol) of 3-phenyl-2-propene-1-ylamine were dissolved in 10 ml of DMF. 129 mg (0.675 mmol) of WSC hydrochloride was added to the obtained solution under cooling with ice, and they were stirred at room temperature overnight. After the concentration under reduced pressure, the reaction mixture was diluted with ethyl acetate and then washed with 1 N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (dichloromethane/methanol=50/1 to 10/1) to obtain the title compound. under cooling with ice, and they After the concentration under reduced pressure the reaction mixture was diluted with ethyl acetate washed with 1 N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution The organic layer was dried over anhydrous magnesium sulfate concentrated under reduced pressure The residue was purified by the silica gel chromatography (dichloromethane/methanol=50/1 to 10/1)

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

Procedure: 110 mg (0.243 mmol) of 4-(3-chlorophenyl)-6-[(2-cyclohexylethoxy)methyl]-2-phenyl-1,4-dihydropyrimidine-5-carboxylic acid and 38.8 mg (0.292 mmol) of cinnamylamine were dissolved in 10 ml of dichloromethane. 69.9 mg (0.365 mmol) of WSC hydrochloride and 37.2 mg (0.243 mmol) of HOBT were added to the obtained solution under cooling with ice, and they were stirred at room temperature for 3 hours. The reaction mixture was diluted with dichloromethane and then washed with saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1 to 1/1) to obtain the title compound. under cooling with ice, and they washed with saturated aqueous sodium hydrogencarbonate solution The organic layer was dried over anhydrous sodium sulfate concentrated under reduced pressure The residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1 to 1/1)

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

Procedure: Aminomethyl styrene resin was prepared from chloromethyl styrene resin (Polumer Laboratories, PL-CMS Resin, 1.0 meq/g) using the procedure of Weinshenker. Weinshenker, N. M.; Shen, C. M.; Wong, J. Y., Organic Synthesis, vol. 56, pp. 95-99. The aminomethyl resin was coupled with N-(Fmoc)glycine using a procedure similar to that described in Example 7. The Fmoc group was removed using a procedure similar to that described in Example 8. This sequence was repeated three times to give the title compound, which has three glycine residues attached to the polystyrene resin. , Organic Synthesis, vol. 56 The Fmoc group was removed

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-cinnamyl phthalimide (3 mmol) was mixed with 65% hydrazine hydrate (6 mmol, 2 equiv) and MeOH (10 ml), and the mixture was heated at 70° C. for 2 h. After the solvent was removed by a rotary evaporator, the solid residue was treated with 1N NaOH (30 ml), and the resulting mixture was extracted with EtOAc (4×50 ml) and dried. Evaporation of the solvent under reduced pressure afforded the crude product, which was purified by flash silica gel column chromatography (eluting with 5-20% MeOH in DCM) to give cinnamyl amine. After the solvent was removed by a rotary evaporator the solid residue was treated with 1N NaOH (30 ml) the resulting mixture was extracted with EtOAc (4×50 ml) dried Evaporation of the solvent under reduced pressure afforded the crude product, which was purified by flash silica gel column chromatography (eluting with 5-20% MeOH in DCM)

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-cinnamyl phthalimide (3 mmol) was mixed with 65% hydrazine hydrate (6 mmol, 2 equiv) and MeOH (10 mL), and the mixture was heated at 70° C. for 2 h. After the solvent was removed by a rotary evaporator, the solid residue was treated with 1 N NaOH (30 mL), and the resulting mixture was extracted with EtOAc (4×50 mL) and dried. Evaporation of the solvent under reduced pressure afforded the crude product, which was purified by flash silica gel column chromatography (eluting with 5-20% MeOH in DCM) to give cinnamyl amine. Compound 117 (white solid) was obtained at 30% yield, and compound 119 (off-white solid) was obtained at 80% yield. Identity was confirmed by 1H NMR (400 MHz, CD3OD). After the solvent was removed by a rotary evaporator the solid residue was treated with 1 N NaOH (30 mL) the resulting mixture was extracted with EtOAc (4×50 mL) dried Evaporation of the solvent under reduced pressure afforded the crude product, which was purified by flash silica gel column chromatography (eluting with 5-20% MeOH in DCM)

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

Procedure: 93 mg (0.30 mmol) of 4-(3-chlorophenyl)-2,6-dimethyl-5-nitro-1,4-dihydropyridine-3-carboxylic acid, 100 mg (0.75 mmol) of cinnamylamine, 138 mg (0.54 mmol) of 2-chloro-1-methylpyridinium iodide and 0.15 ml (1.08 mmol) of triethylamine were stirred in 5 ml of DMF at room temperature for 2 days. DMF was evaporated under reduced pressure. Ethyl acetate was added to the reaction mixture. After washing with 1 N hydrochloric acid, the organic layer was dried over anhydrous sodium sulfate. After the concentration under reduced pressure, the residue was purified by the silica gel chromatography (hexane/ethyl cetate=4/1) to obtain the title compound. DMF was evaporated under reduced pressure Ethyl acetate was added to the reaction mixture After washing with 1 N hydrochloric acid the organic layer was dried over anhydrous sodium sulfate After the concentration under reduced pressure the residue was purified by the silica gel chromatography (hexane/ethyl cetate=4/1)

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

Procedure: 3.06 g (23.0 mmol) of cinnamylamine, 2.32 ml (30.1 mmol) of ketene dimer and 0.321 ml (2.30 mmol) of triethylamine were heated at 70° C. under stirring in 23 ml of toluene for 3 hours. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture. After the extraction with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain the title compound. After the extraction with ethyl acetate the organic layer was dried over anhydrous sodium sulfate concentrated under reduced pressure

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

Procedure: 12.34 g (0.048 mol) of 2,4-dichlorophenacylimidazole and 6.66 g (0.05 mol) of cinnamylamine were suspended in 100 ml of toluene and the suspension was heated under reflux, using a water separator, until no further water of reaction was separated off. The solvent was removed in vacuo, after which 17.4 g (98% of theory) of a viscous oil were obtained. the suspension was heated under reflux was separated off The solvent was removed in vacuo after which 17.4 g (98% of theory) of a viscous oil were obtained