Hydrochloric Acid → 4-(Morpholin-4-yl)benzoic acid

HRID 1177932Notes

Reaction equation

HRID 1177932 reaction equation
[Li+].[OH-].C[O:4][C:5](=[O:18])[C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1.O.Cl>C1COCC1.O>[N:12]1([C:9]2[CH:8]=[CH:7][C:6]([C:5]([OH:18])=[O:4])=[CH:11][CH:10]=2)[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 5178200Methyl 4-Morpholinobenzoate

Product 1

HCID 3452784-(Morpholin-4-yl)benzoic acidYield 86%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

LiOH (92 mg, 0.22 mmol) was added to a stirred solution of 4-morpholin-4-yl-benzoic acid methyl ester (162 mg, 0.73 mmol) in THF:H2O (1:1, 4 mL), and the resulting mixture was stirred at room temperature for 20 hrs. The reaction mixture was concentrated under reduced pressure to get the residue. Cold water was then added and acidified it with 10% aqueous HCl, filtered the solid precipitated to afford 130 mg (86% yield) of 4-morpholin-4-yl-benzoic acid. 1H NMR (DMSO-d6): δ 12.4 (s, 1H), 7.8 (d, 2H), 7.0 (d, 2H), 3.76 (t, 4H), 3.28 (t, 4H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto get the residue
  3. filtrationfiltered the solid
  4. customprecipitated

Sources & evidence

ORD record
ord-da30a61e5ec542ec9756409eebb00874
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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