Morpholine → Ethyl 4-(morpholin-4-yl)benzoate

HRID 2120267Notes

Reaction equation

HRID 2120267 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.F[C:8]1[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=1.FC1C=CC(C([O-])=O)=CC=1>O>[CH2:15]([O:14][C:12](=[O:13])[C:11]1[CH:17]=[CH:18][C:8]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[CH:9][CH:10]=1)[CH3:16]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 30140952365-27-7

Product 1

HCID 2763462Ethyl 4-(morpholin-4-yl)benzoateYield 97.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of morpholine (12 g, 0.14 mol) and ethyl 4-fluorobenzoate (8 g, 0.04 mol) is heated at 120° C. The conversion of the 4-fluorobenzoate is complete after 24 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 9.2 g of pure 4-(4-morpholinyl) benzoic acid ethyl ester after recrystallisation from aqueous ethanol (50%, v/v). Yield: 89%. m.p. 82-83° C.; MS 235 (100, M+); H1 NMR (CDCl3): δ 7.93 (d, 21H), 6.86 (dd, 2H), 4.33 (q, 2H), 3.85 (t, 4H), 3.28 (t, 4H), 1.37 (t, 311); C13 NMR (CDCl3): δ 166.57, 154.14, 131.14, 120.70, 113.46, 66.60, 60.39, 47.75, 14.40.

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-e7a40d2246a249f0ab60e0df7701eae0
Source dataset
uspto-grants-2004_02
Patent number
US06689882B2

Reaction notes

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