Morpholine → Methyl 4-Morpholinobenzoate

HRID 1177931Notes

Reaction equation

HRID 1177931 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:7][O:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13](F)=[CH:12][CH:11]=1>O>[CH3:7][O:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 67878Methyl 4-fluorobenzoate

Product 1

HCID 5178200Methyl 4-MorpholinobenzoateYield 234.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of morpholine (996 mg, 1 mL, 11.4 mmol) and 4-fluoro benzoic acid methyl ester (500 mg, 0.32 mmol) was stirred with heating at 120° C. for 48 hrs. Cold water then added, filtered the solid precipitated to afford 166 mg (23.15% yield) of 4-morpholin-4-yl-benzoic acid methyl ester. 1H NMR (CDCl3): δ 8.0 (d, 2H), 6.9 (d, 2H), 3.9 (m, 7H), 3.3 (t, 4H).

Workup

  1. filtrationfiltered the solid
  2. customprecipitated

Sources & evidence

ORD record
ord-5b9aa1117d4d4e7590ffdf1decdb6178
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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