Ethanol → 4-Phenylmorpholin-3-ON

HRID 415934

Reaktionsgleichung

Reaktionsgleichung von HRID 415934
[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

Komponenten

6

Edukt 4

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

Produkt 1

HCID 51530804-Phenylmorpholin-3-ONAusbeute 62,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
41 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8de1a50e378044429374962f4aed65ab
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088794B2

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