2-(2-hydroxyethylamino)-1-phenylethanol

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 mixture of N-(4-chlorobenzyl)-2-(chloromethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide (75 mg, 0.190 mmol), α-2-hydroxyethylaminomethyl-benzyl alcohol (Bulletin of the Chemical Society of Japan, 56(1), 212-18; 1983)(51 mg, 0.28 mmol) and diisopropylethylamine (50 μL, 0.29 mmol) in dry DMF (4.0 mL) was heated to 60° C. for 18 hours. The solution was then diluted with water (20 mL). The resulting precipitate was collected by filtration and the collected solid was dried in vacuo at 60° C. to provide the titled compound (92 mg) as a white solid. The resulting precipitate was collected by filtration the collected solid was dried in vacuo at 60° C.

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

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

Procedure: A mixture of N-(4-chlorobenzyl)-2-(chloromethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide (75 mg, 0.190 mmol), α-2-hydroxyethylaminomethyl-benzyl alcohol (Bulletin of the Chemical Society of Japan, 56(1), 212-18; 1983)(51 mg, 0.28 mmol) and diisopropylethylamine (50 μL, 0.29 mmol) in dry DMF (4.0 mL) was heated to 60° C. for 18 hours. The solution was then diluted with water (20 mL). The resulting precipitate was collected by filtration and the collected solid was dried in vacuo at 60° C. to provide the titled compound (92 mg) as a white solid. The resulting precipitate was collected by filtration the collected solid was dried in vacuo at 60° C.

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

Procedure: N-(2'-hydroxy-2'-phenylethyl)-ethanolamine (5.3 g.) was dissolved in 6N hydrochloric acid (100 ml.) and the solution heated at 110° for 4 hours. The mixture was basified with sodium hydroxide solution and extracted into ether. The extract was washed with water, dried over anhydrous sodium sulphate and evaporated to give a crude sample of title compound (Ig.) as an orange oil. the solution heated at 110° for 4 hours extracted into ether The extract was washed with water dried over anhydrous sodium sulphate evaporated

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

Procedure: Styrene oxide (1.2 g.), ethanolamine (0.6 g.) and water (0.05 g.) were heated at 70° with stirring for 24 hours. The mixture was cooled, evacuated and the oil formed triturated with ether to give title compound (550 mg.) m.p 93.5° - 95°. The mixture was cooled evacuated the oil formed triturated with ether

Conditions: temp:125.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of styrene oxide (2.40 g, 0.020 mole) and ethanolamine (1.22 g, 0.020 mole) was heated at 125° C. in an oil bath for 2 hr. An NMR analysis showed no styrene oxide remaining. On standing at ambient temperature for 16 hrs, partial solidification occurred. The material was triturated with ethyl acetate, giving a white solid which was collected by filtration and washed with isopropyl ether. A small amount of second crop was obtained from the filtrate for a total of 0.82 g (23%). Recrystallization from ethyl acetate-isopropyl ether gave 0.69 g of a white solid, m.p. 96°-98° C. The material was triturated with ethyl acetate giving a white solid which was collected by filtration washed with isopropyl ether A small amount of second crop was obtained from the filtrate for a total of 0.82 g (23%) Recrystallization from ethyl acetate-isopropyl ether

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

Procedure: A mixture of N-(4-chlorobenzyl)-2-(chloromethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide (75 mg, 0.190 mmol), α-2-hydroxyethylaminomethyl-benzyl alcohol (Bulletin of the Chemical Society of Japan, 56(1), 212-18; 1983)(51 mg, 0.28 mmol) and diisopropylethylamine (50 μL, 0.29 mmol) in dry DMF (4.0 mL) was heated to 60° C. for 18 hours. The solution was then diluted with water (20 mL). The resulting precipitate was collected by filtration and the collected solid was dried in vacuo at 60° C. to provide the titled compound (92 mg) as a white solid. The resulting precipitate was collected by filtration the collected solid was dried in vacuo at 60° C.