3-Fluoroaniline → HCID 17982610, compound

HRID 2246811Notes

Reaction equation

HRID 2246811 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[Cl:9][C:10]1(Cl)[CH2:15][O:14][CH2:13][CH2:12][O:11]1>>[Cl:9][CH2:10][CH2:15][O:14][CH2:13][C:12]([NH:5][C:4]1[CH:6]=[CH:7][CH:8]=[C:2]([F:1])[CH:3]=1)=[O:11]

Participants

3

Reactant 2

HCID 97423-FluoroanilineHCID 124243252,2-Dichloro-1,4-dioxane

Product 1

HCID 17982610HCID 17982610, compound

Conditions

Temperature
100 °C

Procedure

A mixture of 12.0 g (108 mmol) of 3-fluoraniline and 16 g of 2-chlorodioxene (contains 6% of 2,2-dichlorodioxane) is heated at 100° C. for 24 hours. The mixture is allowed to cool, and excess 2-chlorodioxene is removed under reduced pressure, giving 25 g of 2-(2-chloroethoxy)-N-(3-fluorophenyl)acetamide as brown oil; ESI 232. This oil is dissolved in 400 ml of acetonitrile, and 84.7 g (260 mmol) of caesium carbonate are added. The suspension formed is stirred at room temperature for 18 hours. The reaction mixture is filtered, and the filtrate is evaporated, giving 21.0 g of 4-(3-fluorophenyl)morpholin-3-one as brown oil; ESI 196. 1H-NMR (d6-DMSO): δ=3.77 (t, J=5 Hz; 2H), 3.97 (t, J=5 Hz; 2H), 4.23 (s; 2H), 7.11 (dddd, J1=8 Hz, J2=8 Hz, J3=2 Hz, J4=0.5 Hz, 1H), 7.26 (ddd, J1=8 Hz, J2=2 Hz, J3=0.5 Hz, 1H), 7.34 (ddd, J1=10 Hz, J2=2 Hz, J3=2 Hz, 1H), 7.45 (ddd, J1=8 Hz, J2=8 Hz, J3=7 Hz, 1H).

Workup

  1. temperatureto cool
  2. customexcess 2-chlorodioxene is removed under reduced pressure

Sources & evidence

ORD record
ord-f995fe82a4c44c87bb738429d8abb470
Source dataset
uspto-grants-2010_03
Patent number
US07687624B2

Reaction notes

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