Morpholine → 4-Morpholinoacetophenone

HRID 2120268Notes

Reaction equation

HRID 2120268 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.F[C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[CH:10][CH:9]=1>O>[N:1]1([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[CH:10][CH:9]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 98284'-Fluoroacetophenone2×

Product 1

HCID 383624-MorpholinoacetophenoneYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of morpholine (3.2 g, 37 mmol) and 1-(4-fluorophenyl) ethanone (1.5 g, 11 mmol) is heated at 120° C. The conversion of the 1-(4-fluorophenyl) ethanone is complete after 10 hours. Water (10 ml) is than added into the reaction mixture. The precipitate is filtered off, washed with water and dried under vacuum (30° C.) to give 2.1 g of the title-compound. Yield: 93%; m.p. 95-96° C.; MS 205 (100, M+); H1 NMR (CDCl3): δ 7.99 (d, 2H), 6.86 (d, 2H), 3.86 (t, 4H), 3.30 (t, 4H), 2.53 (s, 3H); C13 NMR (CDCl3): δ 196.76, 154.43, 130.55, 128.36, 113.48, 101.16, 66.7, 47.73, 26.37.

Workup

  1. additionthan added into the reaction mixture
  2. filtrationThe precipitate is filtered off
  3. washwashed with water
  4. customdried under vacuum (30° C.)

Sources & evidence

ORD record
ord-77a2148ad66645e7b2237cb1cc112436
Source dataset
uspto-grants-2004_02
Patent number
US06689882B2

Reaction notes

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