| 62.5% |
With sodium hydroxide; In ethanol; water; at 0 - 41℃; for 2h;pH 12 - 12.5;Product distribution / selectivity; |
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 niL 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 X 60 mL cold water). The solids were dried at 50 0C 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). |
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With sodium hydroxide; In ethanol; water; |
1st Step: 4-phenyl-3-morpholinone (VIII) In a 26-litre tank, 1.65 kg (12.0 mol) of 2-anilinoethanol are dissolved at room temperature in 1.53 l of ethanol and subsequently admixed with 4.58 l of water with stirring. The solution is heated to 38 C. 4.07 kg (3.0 equivalents) of chloroacetyl chloride and 6.60 kg of 45% sodium hydroxide solution (6.2 equivalents) are then added simultaneously at an internal temperature of 38 to 43 C. within 60 to 80 minutes, so that the pH is kept between 12 and 12.5. The mixture is stirred at a pH of 12 to 12.5 for 10 minutes, then cooled to 2 C. and stirred at this temperature for 30 minutes. The precipitated product is filtered off and washed twice with 3.3 kg each time of demineralized water at 2 C. |
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With sodium hydroxide; In water; isopropyl alcohol; at 35 - 40℃; for 1h;pH 12.5 - 13.0; |
100 ml IPA and 100 g 2-phenylaminoethanol were added to RBF at 25C to 35C followed by stirring for 10 min. To the reaction mass 100 ml water added and temperature raised to 35C to 40C. Further NaOH solution (180.78 g NaOH + 350 mL water) was added in pressure equalizing funnel. Similarly 246.98 g chloroacetyl chloride was added in another pressure equalizing dropping funnel. The NaOH solution and chloroacetyl chloride were added simultaneously at such a rate that pH maintained between 12.5-13.0. The reaction mass was stirred for 60 min. 35C to 40C water to afford title compound as 4-Phenylmorpholin-3-one (A) |
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With sodium hydroxide; In water; isopropyl alcohol; at 25 - 40℃; for 1h;pH 12.5-13.0; |
100 ml IPA and 100 g 2-phenylaminoethanol were added to RBF at 25 C. to 35 C. followed by stirring for 10 min. To the reaction mass 100 ml water added and temperature raised to 35 C. to 40 C. Further NaOH solution (180.78 g NaOH+350 mL water) was added in pressure equalizing funnel. Similarly 246.98 g chloroacetyl chloride was added in another pressure equalizing dropping funnel. The NaOH solution and chloroacetyl chloride were added simultaneously at such a rate that pH maintained between 12.5-13.0. The reaction mass was stirred for 60 min. 35 C. to 40 C. water to afford title compound as 4-Phenylmorpholin-3-one (A) |
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With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 60℃; for 4h; |
Chloroacetyl chloride was added indrop wise manner in a previously cooled round bottom flaskcontaining INT-a (0.01 mol), DMF and K2CO3 (0.02 mol)maintain the temperature at 0 C. After completion of theaddition, raise the temperature at 60 C and maintain further 4 hprogress of the reaction was monitored on TLC (Scheme-I). |
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