Ethanol → 4-Phenylmorpholin-3-ON

HRID 415929

反応式

HRID 415929 の反応式
[NH:1]([CH2:8][CH2:9][OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCO.[OH-].[Na+].Cl[CH2:17][C:18](Cl)=[O:19]>O>[C:2]1([N:1]2[CH2:8][CH2:9][O:10][CH2:17][C:18]2=[O:19])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 702EthanolHCID 6577Chloroacetyl chlorideHCID 14798Sodium Hydroxide2 回HCID 31235N-(2-Hydroxyethyl)aniline

生成物 1

HCID 51530804-Phenylmorpholin-3-ON収率 62.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
41 °C

実験手順

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).

後処理

  1. temperaturewas maintained between 12 and 12.5
  2. additionAfter the addition
  3. temperaturethe solution was cooled to 0° C.
  4. customThe solids were collected
  5. washwashed with water (2×60 mL cold water)
  6. customThe solids were dried at 50° C. at 0.2 mm Hg for 36 h

出典と根拠

ORDレコード
ord-ac250de3967c42fd8658a452845bfeeb
出典データセット
uspto-grants-2012_01
特許番号
US08088794B2

関連ノート

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