N-(2-phenylethyl)formamide

Conditions: temp:180.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 250 mL round bottom flask equipped with stir bar, reflux condenser, and an addition funnel is charged with phosphorus pentoxide (7.07 g) and polyphosphoric acid in a 10.5:1 weight ratio. The mixture is stirred and heated at approximately 180° C. for about 1 hour, then cooled to approximately 150° C. The cooled, crude phenethylformamide prepared as described above is added dropwise to this mixture. On complete addition the reaction is heated and stirred at approximately 170° C. overnight. The mixture is cooled to room temperature and diluted with water (300 mL), washed with diethyl ether (150 mL) and cooled in an acetone/dry ice bath while the pH is adjusted to 9 with saturated potassium hydroxide. The aqueous solution is extracted with ether (3×150 mL) and the pooled organics are dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield an oil that is further purified via Kugelrohr distillation (70° C., 1 mm Hg) to give the compound of formula 2. A 250 mL round bottom flask equipped reflux condenser, and an addition funnel The mixture is stirred cooled to approximately 150° C above is added dropwise to this mixture On complete addition the reaction is heated stirred at approximately 170° C. overnight The mixture is cooled to room temperature washed with diethyl ether (150 mL) cooled in an acetone/dry ice bath while the pH The aqueous solution is extracted with ether (3×150 mL) the pooled organics are dried over magnesium sulfate filtered concentrated under reduced pressure to yield an oil that is further purified via Kugelrohr distillation (70° C., 1 mm Hg)

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

Procedure: This was prepared in an identical manner to the compound described in Description 10 using N-formyl-2-phenylethanamine (95 g), acetylbromide (128 ml), aluminium chloride (288 g) in 1,2-dichloroethane (900 ml). 25 g of the crude produce was chromatographed on Kieselgel 60 (1 Kg). Elution with 1% methanol-chloroform gave the title compound as an oil (18 g). τ(CDCl3) 7.42 (3H, s), 7.1 (2H, t, J=7 Hz), 6.5 (2H, m), 3.45 (1H, broad), 2.7 (2H, d, J=8 Hz) 2.1 (2H, d, J=8 Hz), 1.9 (1H, s). This was prepared in an identical manner to the compound 25 g of the crude produce was chromatographed on Kieselgel 60 (1 Kg) Elution with 1% methanol-chloroform

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

Procedure: Into a 250-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of LiAlH4 (868 mg, 22.84 mmol, 1.50 equiv) in tetrahydrofuran (70 mL). This was followed by the addition of a solution of N-phenethylformamide (2.27 g, 15.23 mmol, 1.00 equiv) in tetrahydrofuran (50 mL) dropwise with stiffing while the resulting solution maintained reflux. The resulting solution was stirred overnight at reflux in an oil bath. The reaction was then quenched by the addition of water. The resulting solution was extracted with 4×30 mL of dichloromethane and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (100:1). This resulted in 1.36 g (34%) of N-methyl-2-phenylethanamine as yellow oil. Into a 250-mL 3-necked round-bottom flask purged maintained with an inert atmosphere of nitrogen maintained reflux at reflux in an oil bath The reaction was then quenched by the addition of water The resulting solution was extracted with 4×30 mL of dichloromethane dried over anhydrous sodium sulfate concentrated under vacuum This resulted in 1.36 g (34%) of N-methyl-2-phenylethanamine as yellow oil

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

Procedure: Into a 250-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of LiAlH4 (868 mg, 22.84 mmol, 1.50 equiv) in tetrahydrofuran (70 mL). This was followed by the addition of a solution of N-phenethylformamide (2.27 g, 15.23 mmol, 1.00 equiv) in tetrahydrofuran (50 mL) dropwise with stiffing while the resulting solution maintained reflux. The resulting solution was stirred overnight at reflux in an oil bath. The reaction was then quenched by the addition of water. The resulting solution was extracted with 4×30 mL of dichloromethane and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (100:1). This resulted in 1.36 g (34%) of N-methyl-2-phenylethanamine as yellow oil. Into a 250-mL 3-necked round-bottom flask purged maintained with an inert atmosphere of nitrogen maintained reflux at reflux in an oil bath The reaction was then quenched by the addition of water The resulting solution was extracted with 4×30 mL of dichloromethane dried over anhydrous sodium sulfate concentrated under vacuum This resulted in 1.36 g (34%) of N-methyl-2-phenylethanamine as yellow oil

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 2-phenylethanamine (1.9 g, 15.70 mmol, 1.00 equiv). This was followed by the addition of ethyl formate (5 g, 67.57 mmol, 4.30 equiv) dropwise with stiffing. The resulting solution was stirred overnight at 50° C. The resulting solution was concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (70:1). This resulted in 2.27 g (97%) of N-phenethylformamide as yellow oil. Into a 100-mL 3-necked round-bottom flask purged maintained with an inert atmosphere of nitrogen The resulting solution was concentrated under vacuum This resulted in 2.27 g (97%) of N-phenethylformamide as yellow oil

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

Procedure: (AS3.091) A mixture of phenylethylformamide (g, 1.5 mmol), triethylamine (6.4 mmol), 4 Å molecular sieves (g), triphosgene (0.8 mmol), and selenium powder (3.0 mmol) in CH2Cl2 was refluxed and worked up as mentioned for 2a. The crude residue thus obtained was purified by silica gel column chromatography (EtOAc/hexanes 2:98) to give 0.96 g (95%) of 2b as an oil. 1H NMR (CDCl3) δ 3.03 (t, 2H, J=6.9 Hz), 3.81 (t, 2H, J=6.9 Hz) 7.20-7.38 (m, 5H); HRMS (EI) calcd for C9H9NSe, 210.9895. found, 210.9892. was refluxed The crude residue thus obtained was purified by silica gel column chromatography (EtOAc/hexanes 2:98)

Conditions: temp:180.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 250 mL round bottom flask equipped with stir bar, reflux condenser, and an addition funnel is charged with phosphorus pentoxide (7.07 g) and polyphosphoric acid in a 10.5:1 weight ratio. The mixture is stirred and heated at approximately 180° C. for about 1 hour, then cooled to approximately 150° C. The cooled, crude phenethylformamide prepared as described above is added dropwise to this mixture. On complete addition the reaction is heated and stirred at approximately 170° C. overnight. The mixture is cooled to room temperature and diluted with water (300 mL), washed with diethyl ether (150 mL) and cooled in an acetone/dry ice bath while the pH is adjusted to 9 with saturated potassium hydroxide. The aqueous solution is extracted with ether (3×150 mL) and the pooled organics are dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield an oil that is further purified via Kugelrohr distillation (70° C., 1 mm Hg) to give the compound of formula 2. A 250 mL round bottom flask equipped reflux condenser, and an addition funnel The mixture is stirred cooled to approximately 150° C above is added dropwise to this mixture On complete addition the reaction is heated stirred at approximately 170° C. overnight The mixture is cooled to room temperature washed with diethyl ether (150 mL) cooled in an acetone/dry ice bath while the pH The aqueous solution is extracted with ether (3×150 mL) the pooled organics are dried over magnesium sulfate filtered concentrated under reduced pressure to yield an oil that is further purified via Kugelrohr distillation (70° C., 1 mm Hg)

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

Procedure: (AS3.091) A mixture of phenylethylformamide (g, 1.5 mmol), triethylamine (6.4 mmol), 4 Å molecular sieves (g), triphosgene (0.8 mmol), and selenium powder (3.0 mmol) in CH2Cl2 was refluxed and worked up as mentioned for 2a. The crude residue thus obtained was purified by silica gel column chromatography (EtOAc/hexanes 2:98) to give 0.96 g (95%) of 2b as an oil. 1H NMR (CDCl3) δ 3.03 (t, 2H, J=6.9 Hz), 3.81 (t, 2H, J=6.9 Hz) 7.20-7.38 (m, 5H); HRMS (EI) calcd for C9H9NSe, 210.9895; found, 210.9892. was refluxed The crude residue thus obtained was purified by silica gel column chromatography (EtOAc/hexanes 2:98)

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

Procedure: (AS3.091) A mixture of phenylethylformamide (g, 1.5 mmol), triethylamine (6.4 mmol), 4 Å molecular sieves (g), triphosgene (0.8 mmol), and selenium powder (3.0 mmol) in CH2Cl2 was refluxed and worked up as mentioned for 2a. The crude residue thus obtained was purified by silica gel column chromatography (EtOAc/hexanes 2:98) to give 0.96 g (95%) of 2b as an oil. 1H NMR (CDCl3) δ 3.03 (t, 2H, J=6.9 Hz), 3.81 (t, 2H, J=6.9 Hz) 7.20-7.38 (m, 5H); HRMS (EI) calcd for C9H9NSe, 210.9895. found, 210.9892. was refluxed The crude residue thus obtained was purified by silica gel column chromatography (EtOAc/hexanes 2:98)

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

Procedure: (AS3.091) A mixture of phenylethylformamide (g, 1.5 mmol), triethylamine (6.4 mmol), 4 Å molecular sieves (g), triphosgene (0.8 mmol), and selenium powder (3.0 mmol) in CH2Cl2 was refluxed and worked up as mentioned for 2a. The crude residue thus obtained was purified by silica gel column chromatography (EtOAc/hexanes 2:98) to give 0.96 g (95%) of 2b as an oil. 1H NMR (CDCl3) δ 3.03 (t, 2H, J=6.9 Hz), 3.81 (t, 2H, J=6.9 Hz) 7.20-7.38 (m, 5H); HRMS (EI) calcd for C9H9NSe, 210.9895. found, 210.9892. was refluxed The crude residue thus obtained was purified by silica gel column chromatography (EtOAc/hexanes 2:98)

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

Procedure: (AS3.091) A mixture of phenylethylformamide (g, 1.5 mmol), triethylamine (6.4 mmol), 4 Å molecular sieves (g), triphosgene (0.8 mmol), and selenium powder (3.0 mmol) in CH2Cl2 was refluxed and worked up as mentioned for 2a. The crude residue thus obtained was purified by silica gel column chromatography (EtOAc/hexanes 2:98) to give 0.96 g (95%) of 2b as an oil. 1H NMR (CDCl3) δ 3.03 (t, 2H, J=6.9 Hz), 3.81 (t, 2H, J=6.9 Hz) 7.20-7.38 (m, 5H); HRMS (EI) calcd for C9H9NSe, 210.9895. found, 210.9892. was refluxed The crude residue thus obtained was purified by silica gel column chromatography (EtOAc/hexanes 2:98)

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

Procedure: Polyphosphoric acid (25 g) and phosphorus pentoxide (5.4 g, 38.0 mmol) were heated to 180° C. over the course of one hour in an oil bath under an argon atmosphere. N-Phenylethylformamide (146) (4.3 g, 28.8 mmol) was then added at 160° C., and the mixture was stirred for 1.5 hours at constant temperature. The mixture was then allowed to cool to room temperature, and water (40 ml) was added. The mixture was subsequently adjusted to pH 10 by careful addition of saturated aqueous NaOH solution. The mixture was then extracted with ether (500 ml), and the organic phase was separated off and dried using NaOH. Evaporation gave a brown oil (2.81 g, 21.4 mmol, 74%). The mixture was then extracted with ether (500 ml) the organic phase was separated off dried Evaporation