2-anilinoethanol

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

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

Conditions: temp:41.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 250-mL flask was charged with 2-anilinoethanol (9.17 ml, 73.2 mmol), 9 mL dry EtOH, an overhead stirrer, a calibrated pH probe, and 27 mL water. An addition funnel was charged with 10 N sodium hydroxide solution (45.4 ml, 454 mmol). The solution was heated to 41° C., and treated with chloracetyl chloride (17.5 ml, 220 mmol) via a syringe pump over 1 h. The sodium hydroxide solution was simultaneously added to the stirring solution so that the pH was maintained between 12 and 12.5. After the addition was complete, the solution was cooled to 0° C. and stirred for 1 h. The solids were collected and washed with water (2×60 mL cold water). The solids were dried at 50° C. at 0.2 mm Hg for 36 h to afford 4-phenylmorpholin-3-one (8.10 g, 62.5% yield). 1H NMR (400 MHz, CHLOROFORM-d) 3.75-3.80 (m, 2 H) 4.02-4.06 (m, 2 H) 4.35 (s, 2 H) 7.27-7.36 (m, 3 H) 7.39-7.46 (m, 2 H). 13C NMR (101 MHz, CHLOROFORM-d) 49.69 (s, 1 C) 64.14 (s, 1 C) 68.57 (s, 1 C) 125.48 (s, 2 C) 127.15 (s, 1 C) 129.30 (s, 2 C) 141.31 (s, 1 C) 166.59 (s, 1 C). was maintained between 12 and 12.5 After the addition the solution was cooled to 0° C. The solids were collected washed with water (2×60 mL cold water) The solids were dried at 50° C. at 0.2 mm Hg for 36 h

Conditions: temp:41.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 250-mL flask was charged with 2-anilinoethanol (9.17 ml, 73.2 mmol), 9 mL dry EtOH, an overhead stirrer, a calibrated pH probe, and 27 mL water. An addition funnel was charged with 10 N sodium hydroxide solution (45.4 ml, 454 mmol). The solution was heated to 41° C., and treated with chloracetyl chloride (17.5 ml, 220 mmol) via a syringe pump over 1 h. The sodium hydroxide solution was simultaneously added to the stirring solution so that the pH was maintained between 12 and 12.5. After the addition was complete, the solution was cooled to 0° C. and stirred for 1 h. The solids were collected and washed with water (2×60 mL cold water). The solids were dried at 50° C. at 0.2 mm Hg for 36 h to afford 4-phenylmorpholin-3-one (8.10 g, 62.5% yield). 1H NMR (400 MHz, CHLOROFORM-d) 3.75-3.80 (m, 2 H) 4.02-4.06 (m, 2 H) 4.35 (s, 2 H) 7.27-7.36 (m, 3 H) 7.39-7.46 (m, 2 H). 13C NMR (101 MHz, CHLOROFORM-d) 49.69 (s, 1 C) 64.14 (s, 1 C) 68.57 (s, 1 C) 125.48 (s, 2 C) 127.15 (s, 1 C) 129.30 (s, 2 C) 141.31 (s, 1 C) 166.59 (s, 1 C). was maintained between 12 and 12.5 After the addition the solution was cooled to 0° C. The solids were collected washed with water (2×60 mL cold water) The solids were dried at 50° C. at 0.2 mm Hg for 36 h

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

Procedure: Trimethylsilyl cyanide (723 μL) was added to a mixture of 4-(trifluoromethyl)benzaldehyde (CAS #455-19-6, 1 g), N-phenylethanolamine (870 mg) and sulfamic acid (28 mg), and the mixture was stirred at room temperature for 20 hours. The reaction solution was partitioned with water and chloroform. The organic layer was dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent:heptane:ethyl acetate=9:1→1:1) to obtain 775 mg of the title compound. The property values of the compound are as follows. The reaction solution was partitioned with water and chloroform The organic layer was dried over anhydrous magnesium sulfate The organic layer was concentrated under reduced pressure The resulting residue was purified by silica gel column chromatography (elution solvent:heptane:ethyl acetate=9:1→1:1)

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

Procedure: The entitled compound (43 mg) was obtained by allowing 40.6 mg of bis(4,4′-(phenylhydroxyboryl)benzyl) ether and 14 mg of phenylglycinol to act in 1 mL of ethanol.

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.283 g of 3-(2-phenyl-2-chloro acetyl) N-methylindole (1 mmole) (H. Nakamura and T. Goto, Heterocyles, 10, 167-170 (1978) and 0.274 g of 2-anilino ethanol (2.0 mmole) were dissolved in 3 ml of dry ethanol and heated in a sealed tube at 80° C. for 8 hours. On cooling the product crystallized out as pale yellow needles which was filtered and dried to yield 0.21 g of N-phenyl indole oxazine Compound 17. On cooling the product crystallized out as pale yellow needles which was filtered dried

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.283 g of 3-(2-phenyl-2-chloro acetyl) N-methylindole (1 mmole) (H. Nakamura and T. Goto, Heterocyles, 10, 167-170 (1978) and 0.274 g of 2-anilino ethanol (2.0 mmole) were dissolved in 3 ml of dry ethanol and heated in a sealed tube at 80° C. for 8 hours. On cooling the product crystallized out as pale yellow needles which was filtered and dried to yield 0.21 g of N-phenyl indole oxazine Compound 17. On cooling the product crystallized out as pale yellow needles which was filtered dried

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.271 g of P-(2-phenyl-2-chloro acetyl) dimethylamino-benzene (1 mmole) and 0.274 g of N-(2 hydroxy ethyl) aniline (2.0 mmole) were dissolved in 3 ml of dry ethanol and heated in a sealed tube at 80° C. for 8 hours. On cooling the product crystallized out as pale yellow needles., which was filtered and dried to yield 0.2 g of N-phenyl oxazine Compound 15. On cooling the product crystallized out as pale yellow needles , which was filtered dried

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

Procedure: 2-anilinoethanol (13.7 g, 0.10 mol) is treated with allyl bromide (18.15 g, 0.15 mol), in the manner as set forth in Example 3, to provide N-allyl-N-(2-hydroxyethyl)benzenamine.

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

Procedure: The mixture consisting of 2 moles (274.4 g) of N-β-hydroxyethylaniline, 140 g of calcium carbonate and 1.2 moles (154.8 g) of 1,3-dichloro-2-propanol in 1 liter of water is heated for 6 hours under water reflux. is heated for 6 hours under water reflux

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

Procedure: The mixture consisting of 2 moles (274.4 g) of N-β-hydroxyethylaniline, 140 g of calcium carbonate and 1.2 moles (154.8 g) of 1,3-dichloro-2-propanol in 1 liter of water is heated for 6 hours under water reflux. is heated for 6 hours under water reflux