3-phenoxypropan-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:

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

Procedure: A solution of 3-phenoxy-1-propanamine (24.2 g, 160 mmol) in 100 mL of 2-propanol is heated to reflux and treated slowly with a solution of 4-(2-bromoethoxy)phenol (17.4 g, 80 mmol) in 150 mL of 2-propanol. The mixture is heated at reflux for 4 days, then cooled and partitioned between ethyl ether and aqueous sodium bicarbonate solution. The organic layer is evaporated and the residue recrystallized from ethanol to give 6.0 g (20%) of product, mp 204-205° C. to reflux The mixture is heated at reflux for 4 days cooled partitioned between ethyl ether and aqueous sodium bicarbonate solution The organic layer is evaporated the residue recrystallized from ethanol

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

Procedure: A solution of 3-phenoxy-1-propanamine (24.2 g, 160 mmol) in 100 mL of 2-propanol is heated to reflux and treated slowly with a solution of 4-(2-bromoethoxy)phenol (17.4 g, 80 mmol) in 150 mL of 2-propanol. The mixture is heated at reflux for 4 days, then cooled and partitioned between ethyl ether and aqueous sodium bicarbonate solution. The organic layer is evaporated and the residue recrystallized from ethanol to give 6.0 g (20%) of product, mp 204-205° C. to reflux The mixture is heated at reflux for 4 days cooled partitioned between ethyl ether and aqueous sodium bicarbonate solution The organic layer is evaporated the residue recrystallized from ethanol

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

Procedure: A solution of 4-methylbenzenepropanoic acid (2.0 g, 12.2 mmol) and triethylamine (4.3 mL, 3.1 g, 30.9 mmol) in 80 mL of tetrahydrofuran is cooled in ice and treated dropwise with isobutyl chloroformate (1.7 mL, 1.8 g, 13.1 mmol). The mixture is stirred for 1 hour, and a solution of 3-phenoxy-1-propanamine (1.9 g, 12.6 mmol) in 10 mL of tetrahydrofuran is added slowly. The mixture is stirred at room temperature for 18 hours, then added to 400 mL of brine. The mixture is acidified with 4.0 N hydrochloric acid and extracted with ethyl acetate. The combined organic layers are washed with brine, dried (anhydrous sodium sulfate), and evaporated. Recrystallization of the residue gives 2.2 g (61%) of the amide intermediate product, mp 101-102° C. The mixture is stirred at room temperature for 18 hours extracted with ethyl acetate The combined organic layers are washed with brine dried (anhydrous sodium sulfate) evaporated Recrystallization of the residue

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

Procedure: A solution of 3-phenoxy-propionamide (1.0 g, 6.0 mmol) in diethyl ether (30 mL) was cooled to 0 C. Lithium aluminum hydride (0.46 g, 12 mmol) was added in portions to the stirring amide solution. The resulting slurry was allowed to warm to rt and stirred for 20 h. The mixture was cooled to 0° C. and carefully quenched by the sequential addition of 0.5 mL of water, followed by 0.5 mL of 3 N sodium hydroxide and 1.5 mL of water. The mixture was stirred for 15 min, then filtered to remove the aluminum salts. The filtrate was collected and the volatile material was removed by a rotary evaporator to give 3-phenoxy-propylamine (0.55 g) as a pale green oil. The mixture was cooled to 0° C. carefully quenched by the sequential addition of 0.5 mL of water The mixture was stirred for 15 min filtered to remove the aluminum salts The filtrate was collected the volatile material was removed by a rotary evaporator

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: A solution of 3-phenoxy-propionamide (1.0 g, 6.0 mmol) in diethyl ether (30 mL) was cooled to 0 C. Lithium aluminum hydride (0.46 g, 12 mmol) was added in portions to the stirring amide solution. The resulting slurry was allowed to warm to rt and stirred for 20 h. The mixture was cooled to 0° C. and carefully quenched by the sequential addition of 0.5 mL of water, followed by 0.5 mL of 3 N sodium hydroxide and 1.5 mL of water. The mixture was stirred for 15 min, then filtered to remove the aluminum salts. The filtrate was collected and the volatile material was removed by a rotary evaporator to give 3-phenoxy-propylamine (0.55 g) as a pale green oil. The mixture was cooled to 0° C. carefully quenched by the sequential addition of 0.5 mL of water The mixture was stirred for 15 min filtered to remove the aluminum salts The filtrate was collected the volatile material was removed by a rotary evaporator