N-(2-phenylethyl)acetamide

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

Procedure: In a 500 ml flame-dried flask, N-phenethyl-acetamide (6.53 g, 40.0 mmol) was dissolved in methylene chloride (65 ml), and acetyl chloride (7.22 g, 92.0 mmol) was added in one portion. The resulting solution was cooled to about 0° C., and aluminum chloride (18.1 g, 136 mmol) was added in portions over about thirty minutes. The solution was stirred for about five minutes at about 0° C., and the ice bath was then removed and the mixture was heated to reflux for about thirty minutes. After cooling to room temperature, the reaction mixture was poured over ice water, stirred for about ten minutes, and then extracted with methylene chloride (2×100 ml). The combined organic extracts were then washed sequentially with water and brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting white solid (7.52 g, 92% yield) was ascertained to be about 90% pure by NMR, and was employed directly without further purification. LRMS ([M+H]+)=206.2. In a 500 ml flame-dried flask the ice bath was then removed the mixture was heated to reflux for about thirty minutes After cooling to room temperature the reaction mixture was poured over ice water stirred for about ten minutes extracted with methylene chloride (2×100 ml) The combined organic extracts were then washed sequentially with water and brine dried over magnesium sulfate filtered concentrated in vacuo

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

Procedure: Eur. J. Org. Chem. 2008, 895-913 describes a process comprising: a) reacting phenylethylamine with chloroacetyl chloride in presence of sodium bicarbonate to obtain 2-chloro-N-phenethylacetamide, b) treating 2-chloro-N-phenethylacetamide with aminoacetaldehyde dimethylacetal to give 2-[2,2-dimethoxyethyl)amino]-N-(2-phenylethyl)acetamide, c) making hydrochloride salt of 2-[(2,2-dimethoxyethyl)amino]-N-(2-phenylethyl)acetamide, and d) cyclising using sulphuric acid to form praziquanamine (i.e.4-oxo-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinoline).

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

Procedure: Triethylamine (1.26 ml, 9.08 mmol), followed by acetyl chloride (0.64 ml, 9.08 mmol) was added to a solution of 2-phenylethylamine (1.04 ml, 8.25 mmol) in dichloromethane (16 ml) at 0° . After 2 hours, the solution was poured into water and extracted thoroughly with ethyl ether. Evaporation of the dried (magnesium sulfate) extracts gave an oil, which was purified on silica using 80% ethyl acetate/hexane. The title amide was obtained as a colorless solid. extracted thoroughly with ethyl ether Evaporation of the dried (magnesium sulfate) extracts gave an oil, which was purified on silica using 80% ethyl acetate/hexane

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

Procedure: In close analogy to the procedure described above, N-phenethyl-acetamide is reacted with phosphorus pentoxide to provide the title compound.

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

Procedure: In close analogy to the procedure described above, phenethylamine is reacted with acetic anhydride to provide the title compound.

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

Procedure: acetylating 2-phenylethylamine of the formula II: ##STR2## with acetic anhydride to protect the amino group and obtain N-acetyl (2-phenyl)ethylamine of the formula III: ##STR3## (b) chlorosulfonating the compound of the formula III with chlorosulfonic acid to obtain 4-(N-acetylamino) ethyl benzenesulfonyl chloride of the formula IV: ##STR4## (c) treating the compound of the formula IV with ammonia to obtain 4-(2-acetylaminoethyl)benzene sulfonamide of the formula V: ##STR5## (d) hydrolysing the compound of the formula V by treating with sodium hydroxide to deprotect the amino group and obtain 4-(2-aminoethyl)benzene sulfonamide of the formula VI: ##STR6## (e) treating the compound of the formula VI with hydrochloric acid to obtain 4-(2-aminoethyl)benzenesulfonamide hydrochloride of the formula VII: ##STR7## (f) purifying the compound of the formula VII by crystallization from methanol.

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

Procedure: In a 500 ml flame-dried flask, N-phenethyl-acetamide (6.53 g, 40.0 mmol) was dissolved in methylene chloride (65 ml), and acetyl chloride (7.22 g, 92.0 mmol) was added in one portion. The resulting solution was cooled to about 0° C., and aluminum chloride (18.1 g, 136 mmol) was added in portions over about thirty minutes. The solution was stirred for about five minutes at about 0° C., and the ice bath was then removed and the mixture was heated to reflux for about thirty minutes. After cooling to room temperature, the reaction mixture was poured over ice water, stirred for about ten minutes, and then extracted with methylene chloride (2×100 ml). The combined organic extracts were then washed sequentially with water and brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting white solid (7.52 g, 92% yield) was ascertained to be about 90% pure by NMR, and was employed directly without further purification. LRMS ([M+H]+)=206.2. In a 500 ml flame-dried flask the ice bath was then removed the mixture was heated to reflux for about thirty minutes After cooling to room temperature the reaction mixture was poured over ice water stirred for about ten minutes extracted with methylene chloride (2×100 ml) The combined organic extracts were then washed sequentially with water and brine dried over magnesium sulfate filtered concentrated in vacuo