4-(4-chlorophenyl)butan-1-amine

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:

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

Procedure: In a similar manner to Example 35, a mixture of 4-chlorobenzaldehyde (5.6 g) and 1-(3-aminopropyl)-2-benzyl-4-methylimidazole (9.2 g) in ethanol (100 ml) was stirred and then reduced with sodium borohydride (1.6 g) to give 3-(2-benzyl-4-methylimidazol-1-yl)-[-(4-chlorobenzyl)propylamine, b.p. 190°-200° C. (0.04 mmHg). Glc and 1H nmr indicated that the product contained 21% of 3-(2-benzyl-5-methylimidazol-1-yl)-N-(4-chlorobenzyl)propylamine.

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

Procedure: In a similar manner to Example 35, a mixture of 4-chlorobenzaldehyde (5.6 g) and 1-(3-aminopropyl)-2-benzyl-4-methylimidazole (9.2 g) in ethanol (100 ml) was stirred and then reduced with sodium borohydride (1.6 g) to give 3-(2-benzyl-4-methylimidazol-1-yl)-[-(4-chlorobenzyl)propylamine, b.p. 190°-200° C. (0.04 mmHg). Glc and 1H nmr indicated that the product contained 21% of 3-(2-benzyl-5-methylimidazol-1-yl)-N-(4-chlorobenzyl)propylamine.

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

Procedure: To a stirred suspension of lithium aluminum hydride (1.84 g, 48.6 mmol) in diethyl ether (50 mL) at ambient temperature was added a solution of 4-(4-chlorophenyl)butanamide in tetrahydrofuran (25 mL), dropwise over 8 minutes. Stirring was continued at ambient temperature for a further 4 hours. The reaction mixture was carefully quenched by sequential slow addition of water (2 mL), 10M sodium hydroxide (0.75 mL), and water (7 mL). After stirring the mixture for 20 minutes, it was extracted with diethyl ether (50 mL). The organic layer was dried over sodium sulfate and concentrated to afford 4-(4-chlorophenyl)butan-1-amine as a light yellow oil (1.36 g, 61%). was continued at ambient temperature for a further 4 hours The reaction mixture was carefully quenched by sequential slow addition of water (2 mL), 10M sodium hydroxide (0.75 mL), and water (7 mL) After stirring the mixture for 20 minutes it was extracted with diethyl ether (50 mL) The organic layer was dried over sodium sulfate concentrated

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

Procedure: To a stirred suspension of lithium aluminum hydride (1.84 g, 48.6 mmol) in diethyl ether (50 mL) at ambient temperature was added a solution of 4-(4-chlorophenyl)butanamide in tetrahydrofuran (25 mL), dropwise over 8 minutes. Stirring was continued at ambient temperature for a further 4 hours. The reaction mixture was carefully quenched by sequential slow addition of water (2 mL), 10M sodium hydroxide (0.75 mL), and water (7 mL). After stirring the mixture for 20 minutes, it was extracted with diethyl ether (50 mL). The organic layer was dried over sodium sulfate and concentrated to afford 4-(4-chlorophenyl)butan-1-amine as a light yellow oil (1.36 g, 61%). was continued at ambient temperature for a further 4 hours The reaction mixture was carefully quenched by sequential slow addition of water (2 mL), 10M sodium hydroxide (0.75 mL), and water (7 mL) After stirring the mixture for 20 minutes it was extracted with diethyl ether (50 mL) The organic layer was dried over sodium sulfate concentrated

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

Procedure: To a stirred suspension of lithium aluminum hydride (1.84 g, 48.6 mmol) in diethyl ether (50 mL) at ambient temperature was added a solution of 4-(4-chlorophenyl)butanamide in tetrahydrofuran (25 mL), dropwise over 8 minutes. Stirring was continued at ambient temperature for a further 4 hours. The reaction mixture was carefully quenched by sequential slow addition of water (2 mL), 10M sodium hydroxide (0.75 mL), and water (7 mL). After stirring the mixture for 20 minutes, it was extracted with diethyl ether (50 mL). The organic layer was dried over sodium sulfate and concentrated to afford 4-(4-chlorophenyl)butan-1-amine as a light yellow oil (1.36 g, 61%). was continued at ambient temperature for a further 4 hours The reaction mixture was carefully quenched by sequential slow addition of water (2 mL), 10M sodium hydroxide (0.75 mL), and water (7 mL) After stirring the mixture for 20 minutes it was extracted with diethyl ether (50 mL) The organic layer was dried over sodium sulfate concentrated

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

Procedure: To a stirred suspension of lithium aluminum hydride (1.84 g, 48.6 mmol) in diethyl ether (50 mL) at ambient temperature was added a solution of 4-(4-chlorophenyl)butanamide in tetrahydrofuran (25 mL), dropwise over 8 minutes. Stirring was continued at ambient temperature for a further 4 hours. The reaction mixture was carefully quenched by sequential slow addition of water (2 mL), 10M sodium hydroxide (0.75 mL), and water (7 mL). After stirring the mixture for 20 minutes, it was extracted with diethyl ether (50 mL). The organic layer was dried over sodium sulfate and concentrated to afford 4-(4-chlorophenyl)butan-1-amine as a light yellow oil (1.36 g, 61%). was continued at ambient temperature for a further 4 hours The reaction mixture was carefully quenched by sequential slow addition of water (2 mL), 10M sodium hydroxide (0.75 mL), and water (7 mL) After stirring the mixture for 20 minutes it was extracted with diethyl ether (50 mL) The organic layer was dried over sodium sulfate concentrated

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

Procedure: A solution of 8.2 gr. (45 moles) of p-chlorophenylbutylamine in 100 ml of acetonitrile is stirred and refluxed. 12.4 gr. (90 mmoles) of potassium carbonate are added thereto, then over one hour a solution of 12 gr. (45 mmoles) of the preceding brominated cetone in 80 ml of acetonitrile. After the end of the addition, reflux is maintained for 1.5 hour. To the medium at room temperature, a solution of 1.8 gr. (48 mmoles) of sodium borohydride in 10 ml of water basified with a drop of 40% aqueus NaOH is dropwise added. The solid is filtered and the filtrate is dry evaporated. The residue is a solid. The latter added to the first one is recrystallized from a 1:1 hexane/cyclohexane mixture. 5.1 gr. (14 mmoles, 31%) of a product are obtained, the melting point of which being 107.8° C. The NMR spectrum confirms the expected structure. refluxed After the end of the addition reflux is maintained for 1.5 hour at room temperature is dropwise added The solid is filtered the filtrate is dry evaporated The latter added to the first one is recrystallized from a 1:1 hexane/cyclohexane mixture

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

Procedure: A solution of 8.2 gr. (45 moles) of p-chlorophenylbutylamine in 100 ml of acetonitrile is stirred and refluxed. 12.4 gr. (90 mmoles) of potassium carbonate are added thereto, then over one hour a solution of 12 gr. (45 mmoles) of the preceding brominated cetone in 80 ml of acetonitrile. After the end of the addition, reflux is maintained for 1.5 hour. To the medium at room temperature, a solution of 1.8 gr. (48 mmoles) of sodium borohydride in 10 ml of water basified with a drop of 40% aqueus NaOH is dropwise added. The solid is filtered and the filtrate is dry evaporated. The residue is a solid. The latter added to the first one is recrystallized from a 1:1 hexane/cyclohexane mixture. 5.1 gr. (14 mmoles, 31%) of a product are obtained, the melting point of which being 107.8° C. The NMR spectrum confirms the expected structure. refluxed After the end of the addition reflux is maintained for 1.5 hour at room temperature is dropwise added The solid is filtered the filtrate is dry evaporated The latter added to the first one is recrystallized from a 1:1 hexane/cyclohexane mixture