2-(2-chloro-4-fluorophenyl)ethanamine

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(2-chloro-4-fluorophenyl)acetamide (400 mg, 2.13 mmol) was diluted with THF (2 mL), placed under nitrogen and cooled to 0° C. LAH (4264 μL, 4.26 mmol) was added dropwise and the reaction was refluxed for 3 hours. The reaction was cooled to 0° C. and quenched with 160 μL of water, 160 μL of 15% NaOH, and 530 μL of water. After stirring for 30 minutes the reaction was filtered and concentrated. The material was purified using a biotage 25 column eluting with 2% NH4OH/10% methanol/DCM to yield 2-(2-chloro-4-fluorophenyl)ethanamine (60 mg, 0.346 mmol, 16.2% yield). the reaction was refluxed for 3 hours The reaction was cooled to 0° C. quenched with 160 μL of water, 160 μL of 15% NaOH, and 530 μL of water was filtered concentrated The material was purified eluting with 2% NH4OH/10% methanol/DCM

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(2-chloro-4-fluorophenyl)acetamide (400 mg, 2.13 mmol) was diluted with THF (2 mL), placed under nitrogen and cooled to 0° C. LAH (4264 μL, 4.26 mmol) was added dropwise and the reaction was refluxed for 3 hours. The reaction was cooled to 0° C. and quenched with 160 μL of water, 160 μL of 15% NaOH, and 530 μL of water. After stirring for 30 minutes the reaction was filtered and concentrated. The material was purified using a biotage 25 column eluting with 2% NH4OH/10% methanol/DCM to yield 2-(2-chloro-4-fluorophenyl)ethanamine (60 mg, 0.346 mmol, 16.2% yield). the reaction was refluxed for 3 hours The reaction was cooled to 0° C. quenched with 160 μL of water, 160 μL of 15% NaOH, and 530 μL of water was filtered concentrated The material was purified eluting with 2% NH4OH/10% methanol/DCM

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(2-chloro-4-fluorophenyl)acetamide (400 mg, 2.13 mmol) was diluted with THF (2 mL), placed under nitrogen and cooled to 0° C. LAH (4264 μL, 4.26 mmol) was added dropwise and the reaction was refluxed for 3 hours. The reaction was cooled to 0° C. and quenched with 160 μL of water, 160 μL of 15% NaOH, and 530 μL of water. After stirring for 30 minutes the reaction was filtered and concentrated. The material was purified using a biotage 25 column eluting with 2% NH4OH/10% methanol/DCM to yield 2-(2-chloro-4-fluorophenyl)ethanamine (60 mg, 0.346 mmol, 16.2% yield). the reaction was refluxed for 3 hours The reaction was cooled to 0° C. quenched with 160 μL of water, 160 μL of 15% NaOH, and 530 μL of water was filtered concentrated The material was purified eluting with 2% NH4OH/10% methanol/DCM

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(2-chloro-4-fluorophenyl)acetamide (400 mg, 2.13 mmol) was diluted with THF (2 mL), placed under nitrogen and cooled to 0° C. LAH (4264 μL, 4.26 mmol) was added dropwise and the reaction was refluxed for 3 hours. The reaction was cooled to 0° C. and quenched with 160 μL of water, 160 μL, of 15% NaOH, and 530 μL of water. After stirring for 30 minutes the reaction was filtered and concentrated. The material was purified using a biotage 25 column eluting with 2% NH4OH/10% methanol/DCM to yield 2-(2-chloro-4-fluorophenyl)ethanamine (60 mg, 0.346 mmol, 16.2% yield). the reaction was refluxed for 3 hours The reaction was cooled to 0° C. quenched with 160 μL of water, 160 μL, of 15% NaOH, and 530 μL of water was filtered concentrated The material was purified eluting with 2% NH4OH/10% methanol/DCM

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(2-chloro-4-fluorophenyl)acetamide (400 mg, 2.13 mmol) was diluted with THF (2 mL), placed under nitrogen and cooled to 0° C. LAH (4264 μL, 4.26 mmol) was added dropwise and the reaction was refluxed for 3 hours. The reaction was cooled to 0° C. and quenched with 160 μL of water, 160 μL, of 15% NaOH, and 530 μL of water. After stirring for 30 minutes the reaction was filtered and concentrated. The material was purified using a biotage 25 column eluting with 2% NH4OH/10% methanol/DCM to yield 2-(2-chloro-4-fluorophenyl)ethanamine (60 mg, 0.346 mmol, 16.2% yield). the reaction was refluxed for 3 hours The reaction was cooled to 0° C. quenched with 160 μL of water, 160 μL, of 15% NaOH, and 530 μL of water was filtered concentrated The material was purified eluting with 2% NH4OH/10% methanol/DCM

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

Procedure: Sodium borohydride (1.73 g, 45.51 mmol) was added portionwise to a solution of 2-chloro-4-fluorophenylacetonitrile (1.04 g, 6.15 mmol) and cobalt (II) chloride hexahydrate (2.18 g, 9.22 mmol) in methanol (30 mL) and the mixture was stirred at room temperature for 3 hours. The suspension was then filtered though Celite®, concentrated in vacuo and the residue was partitioned between 1M hydrochloric acid (40 mL) and dichloromethane (40 mL). The aqueous phase was separated, basified to pH 11 with 1M ammonia solution and extracted with dichloromethane (2×40 mL). The combined organic solution was washed with brine (30 mL), dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with dichloromethane:methanol:0.88 ammonia, 100:0:0 to 98:2:0.2, to afford the title compound as a yellow oil, 350 mg. The suspension was then filtered though Celite® concentrated in vacuo the residue was partitioned between 1M hydrochloric acid (40 mL) and dichloromethane (40 mL) The aqueous phase was separated extracted with dichloromethane (2×40 mL) The combined organic solution was washed with brine (30 mL) dried over magnesium sulfate concentrated in vacuo The residue was purified by column chromatography on silica gel eluting with dichloromethane

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

Procedure: Sodium borohydride (1.73 g, 45.51 mmol) was added portionwise to a solution of 2-chloro-4-fluorophenylacetonitrile (1.04 g, 6.15 mmol) and cobalt (II) chloride hexahydrate (2.18 g, 9.22 mmol) in methanol (30 mL) and the mixture was stirred at room temperature for 3 hours. The suspension was then filtered though Celite®, concentrated in vacuo and the residue was partitioned between 1M hydrochloric acid (40 mL) and dichloromethane (40 mL). The aqueous phase was separated, basified to pH 11 with 1M ammonia solution and extracted with dichloromethane (2×40 mL). The combined organic solution was washed with brine (30 mL), dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with dichloromethane:methanol:0.88 ammonia, 100:0:0 to 98:2:0.2, to afford the title compound as a yellow oil, 350 mg. The suspension was then filtered though Celite® concentrated in vacuo the residue was partitioned between 1M hydrochloric acid (40 mL) and dichloromethane (40 mL) The aqueous phase was separated extracted with dichloromethane (2×40 mL) The combined organic solution was washed with brine (30 mL) dried over magnesium sulfate concentrated in vacuo The residue was purified by column chromatography on silica gel eluting with dichloromethane

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(2-chloro-4-fluorophenyl)acetamide (400 mg, 2.13 mmol) was diluted with THF (2 mL), placed under nitrogen and cooled to 0° C. LAH (4264 μL, 4.26 mmol) was added dropwise and the reaction was refluxed for 3 hours. The reaction was cooled to 0° C. and quenched with 160 μL of water, 160 μL of 15% NaOH, and 530 μL of water. After stirring for 30 minutes the reaction was filtered and concentrated. The material was purified using a biotage 25 column eluting with 2% NH4OH/10% methanol/DCM to yield 2-(2-chloro-4-fluorophenyl)ethanamine (60 mg, 0.346 mmol, 16.2% yield). the reaction was refluxed for 3 hours The reaction was cooled to 0° C. quenched with 160 μL of water, 160 μL of 15% NaOH, and 530 μL of water was filtered concentrated The material was purified eluting with 2% NH4OH/10% methanol/DCM

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(2-chloro-4-fluorophenyl)acetamide (400 mg, 2.13 mmol) was diluted with THF (2 mL), placed under nitrogen and cooled to 0° C. LAH (4264 μL, 4.26 mmol) was added dropwise and the reaction was refluxed for 3 hours. The reaction was cooled to 0° C. and quenched with 160 μL of water, 160 μL of 15% NaOH, and 530 μL of water. After stirring for 30 minutes the reaction was filtered and concentrated. The material was purified using a biotage 25 column eluting with 2% NH4OH/10% methanol/DCM to yield 2-(2-chloro-4-fluorophenyl)ethanamine (60 mg, 0.346 mmol, 16.2% yield). the reaction was refluxed for 3 hours The reaction was cooled to 0° C. quenched with 160 μL of water, 160 μL of 15% NaOH, and 530 μL of water was filtered concentrated The material was purified eluting with 2% NH4OH/10% methanol/DCM

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(2-chloro-4-fluorophenyl)acetamide (400 mg, 2.13 mmol) was diluted with THF (2 mL), placed under nitrogen and cooled to 0° C. LAH (4264 μL, 4.26 mmol) was added dropwise and the reaction was refluxed for 3 hours. The reaction was cooled to 0° C. and quenched with 160 μL of water, 160 μL, of 15% NaOH, and 530 μL of water. After stirring for 30 minutes the reaction was filtered and concentrated. The material was purified using a biotage 25 column eluting with 2% NH4OH/10% methanol/DCM to yield 2-(2-chloro-4-fluorophenyl)ethanamine (60 mg, 0.346 mmol, 16.2% yield). the reaction was refluxed for 3 hours The reaction was cooled to 0° C. quenched with 160 μL of water, 160 μL, of 15% NaOH, and 530 μL of water was filtered concentrated The material was purified eluting with 2% NH4OH/10% methanol/DCM

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

Procedure: Sodium borohydride (1.73 g, 45.51 mmol) was added portionwise to a solution of 2-chloro-4-fluorophenylacetonitrile (1.04 g, 6.15 mmol) and cobalt (II) chloride hexahydrate (2.18 g, 9.22 mmol) in methanol (30 mL) and the mixture was stirred at room temperature for 3 hours. The suspension was then filtered though Celite®, concentrated in vacuo and the residue was partitioned between 1M hydrochloric acid (40 mL) and dichloromethane (40 mL). The aqueous phase was separated, basified to pH 11 with 1M ammonia solution and extracted with dichloromethane (2×40 mL). The combined organic solution was washed with brine (30 mL), dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with dichloromethane:methanol:0.88 ammonia, 100:0:0 to 98:2:0.2, to afford the title compound as a yellow oil, 350 mg. The suspension was then filtered though Celite® concentrated in vacuo the residue was partitioned between 1M hydrochloric acid (40 mL) and dichloromethane (40 mL) The aqueous phase was separated extracted with dichloromethane (2×40 mL) The combined organic solution was washed with brine (30 mL) dried over magnesium sulfate concentrated in vacuo The residue was purified by column chromatography on silica gel eluting with dichloromethane