2-(2-phenylethoxy)acetaldehyde

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: β-Alanine (0.6 g) was added to a solution of [2-phenylethoxy]acetaldehyde (8.0 g) and malononitrile (3.5 g) in ethanol (100 ml). The mixture was stirred at room temperature for 3 hours. The solid was filtered off, washed with fresh ethanol and dried to yield the subtitled compound (5.85g, 54%). The solid was filtered off washed with fresh ethanol dried

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

Procedure: β-Alanine (0.6 g) was added to a solution of [2-phenylethoxy]acetaldehyde (8.0 g) and malononitrile (3.5 g) in ethanol (100 ml). The mixture was stirred at room temperature for 3 hours. The solid was filtered off, washed with fresh ethanol and dried to yield the subtitled compound (5.85g, 54%). The solid was filtered off washed with fresh ethanol dried

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

Procedure: β-Alanine (0.6 g) was added to a solution of [2-phenylethoxy]acetaldehyde (8.0 g) and malononitrile (3.5 g) in ethanol (100 ml). The mixture was stirred at room temperature for 3 hours. The solid was filtered off, washed with fresh ethanol and dried to yield the subtitled compound (5.85 g, 54%). The solid was filtered off washed with fresh ethanol dried

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

Procedure: To a mixture of 2-[4-(benzoxazol-2-yl)benzyloxy)]ethylamine hydrochloride (0.11 g; 0.38 mmol) dissolved in MeOH (2 ml) and Et3N (0.053 ml; 0.38 mmol) is added dried and powdered 3 Å molecular sieves along with 2-phenylethoxyacetaldehyde (0.11 g; 0.68 mmol). After 1 hour, a 1M THF solution of sodium cyanoborohydride (0.75 ml; 0.75 mmol) is added dropwise. After 2 hours, the reaction mixture is quenched with acetone and 2N HCl and then concentrated in vacuo to dryness. The residue is dissolved in 3 ml 15% NaOH, extracted with Et2O 4×, dried (MgSO4) and concentrated in vacuo to dryness. The residue is purified by column chromatography using 10% MeOH/CH2Cl2. The product is dissolved in EtOH acidified with HCl/EtOH and concentrated to yield N-[2-(4-(benzoxazol-2-yl)benzyloxy)ethyl]-2-(2-phenylethoxy)ethanamine hydrochloride as a white solid. (m.p. 174°-175° C.). dried After 2 hours the reaction mixture is quenched with acetone and 2N HCl concentrated in vacuo to dryness The residue is dissolved in 3 ml 15% NaOH extracted with Et2O 4× dried (MgSO4) concentrated in vacuo to dryness The residue is purified by column chromatography The product is dissolved in EtOH concentrated

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

Procedure: To 2-(2-phenylethoxy)-1-ethanol (0.25 g; 1.5 mmol) [J. Med. Chem., 1570 (1983)] dissolved in DMSO/CH2Cl2 (4 ml/2 ml) is added Et3N (1 ml; 7 mmol) followed by sulfur trioxide pyridine complex (1.2 g; 7.5 mmol). After 10 minutes, the reaction mixture is then diluted with Et2O and washed with brine, 1N HCl, NaHCO3 and brine, dried (MgSO4) and concentrated in vacuo to dryness. The residue is purified by column chromatography using CH2Cl2 to obtain 2-phenylethoxyacetaldehyde which is used directly in Step B. washed with brine, 1N HCl, NaHCO3 and brine dried (MgSO4) concentrated in vacuo to dryness The residue is purified by column chromatography

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

Procedure: To 2-(2-phenylethoxy)-1-ethanol (0.25 g; 1.5 mmol) [J. Med. Chem., 1570 (1983)] dissolved in DMSO/CH2Cl2 (4 ml/2 ml) is added Et3N (1 ml; 7 mmol) followed by sulfur trioxide pyridine complex (1.2 g; 7.5 mmol). After 10 minutes, the reaction mixture is then diluted with Et2O and washed with brine, 1N HCl, NaHCO3 and brine, dried (MgSO4) and concentrated in vacuo to dryness. The residue is purified by column chromatography using CH2Cl2 to obtain 2-phenylethoxyacetaldehyde which is used directly in Step B. washed with brine, 1N HCl, NaHCO3 and brine dried (MgSO4) concentrated in vacuo to dryness The residue is purified by column chromatography

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

Procedure: β-Alanine (0.6 g) was added to a solution of [2-phenylethoxy]acetaldehyde (8.0 g) and malononitrile (3.5 g) in ethanol (100 ml). The mixture was stirred at room temperature for 3 hours. The solid was filtered off, washed with fresh ethanol and dried to yield the subtitled compound (5.85g, 54%). The solid was filtered off washed with fresh ethanol dried

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a mixture of 2-[4-(benzoxazol-2-yl)benzyloxy)]ethylamine hydrochloride (0.11 g; 0.38 mmol) dissolved in MeOH (2 ml) and Et3N (0.053 ml; 0.38 mmol) is added dried and powdered 3 Å molecular sieves along with 2-phenylethoxyacetaldehyde (0.11 g; 0.68 mmol). After 1 hour, a 1M THF solution of sodium cyanoborohydride (0.75 ml; 0.75 mmol) is added dropwise. After 2 hours, the reaction mixture is quenched with acetone and 2N HCl and then concentrated in vacuo to dryness. The residue is dissolved in 3 ml 15% NaOH, extracted with Et2O 4×, dried (MgSO4) and concentrated in vacuo to dryness. The residue is purified by column chromatography using 10% MeOH/CH2Cl2. The product is dissolved in EtOH acidified with HCl/EtOH and concentrated to yield N-[2-(4-(benzoxazol-2-yl)benzyloxy)ethyl]-2-(2-phenylethoxy)ethanamine hydrochloride as a white solid. (m.p. 174°-175 ° C.). dried After 2 hours the reaction mixture is quenched with acetone and 2N HCl concentrated in vacuo to dryness The residue is dissolved in 3 ml 15% NaOH extracted with Et2O 4× dried (MgSO4) concentrated in vacuo to dryness The residue is purified by column chromatography The product is dissolved in EtOH concentrated

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

Procedure: To a mixture of 2-[4-(benzoxazol-2-yl)benzyloxy)]ethylamine hydrochloride (0.11 g; 0.38 mmol) dissolved in MeOH (2 ml) and Et3N (0.053 ml; 0.38 mmol) is added dried and powdered 3 Å molecular sieves along with 2-phenylethoxyacetaldehyde (0.11 g; 0.68 mmol). After 1 hour, a 1M THF solution of sodium cyanoborohydride (0.75 ml; 0.75 mmol) is added dropwise. After 2 hours, the reaction mixture is quenched with acetone and 2N HCl and then concentrated in vacuo to dryness. The residue is dissolved in 3 ml 15% NaOH, extracted with Et2O 4×, dried (MgSO4) and concentrated in vacuo to dryness. The residue is purified by column chromatography using 10% MeOH/CH2Cl2. The product is dissolved in EtOH acidified with HCl/EtOH and concentrated to yield N-[2-(4-(benzoxazol-2-yl)benzyloxy)ethyl]-2-(2-phenylethoxy)ethanamine hydrochloride as a white solid. (m.p. 174°-175 ° C.). dried After 2 hours the reaction mixture is quenched with acetone and 2N HCl concentrated in vacuo to dryness The residue is dissolved in 3 ml 15% NaOH extracted with Et2O 4× dried (MgSO4) concentrated in vacuo to dryness The residue is purified by column chromatography The product is dissolved in EtOH concentrated

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

Procedure: To a mixture of 2-[4-(benzoxazol-2-yl)benzyloxy)]ethylamine hydrochloride (0.11 g; 0.38 mmol) dissolved in MeOH (2 ml) and Et3N (0.053 ml; 0.38 mmol) is added dried and powdered 3 Å molecular sieves along with 2-phenylethoxyacetaldehyde (0.11 g; 0.68 mmol). After 1 hour, a 1M THF solution of sodium cyanoborohydride (0.75 ml; 0.75 mmol) is added dropwise. After 2 hours, the reaction mixture is quenched with acetone and 2N HCl and then concentrated in vacuo to dryness. The residue is dissolved in 3 ml 15% NaOH, extracted with Et2O 4×, dried (MgSO4) and concentrated in vacuo to dryness. The residue is purified by column chromatography using 10% MeOH/CH2Cl2. The product is dissolved in EtOH acidified with HCl/EtOH and concentrated to yield N-[2-(4-(benzoxazol-2-yl)benzyloxy)ethyl]-2-(2-phenylethoxy)ethanamine hydrochloride as a white solid. (m.p. 174°-175 ° C.). dried After 2 hours the reaction mixture is quenched with acetone and 2N HCl concentrated in vacuo to dryness The residue is dissolved in 3 ml 15% NaOH extracted with Et2O 4× dried (MgSO4) concentrated in vacuo to dryness The residue is purified by column chromatography The product is dissolved in EtOH concentrated