Hydrochloric Acid → 3-[2-(Morpholin-4-yl)ethoxy]benzoic acid

HRID 2168224Notes

Reaction equation

HRID 2168224 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=2)[C:13]([O:15]CC)=[O:14])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl>>[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=2)[C:13]([OH:15])=[O:14])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 58089039Ethyl 3-{[2-(4-morpholinyl)ethyl]oxy}benzoate

Product 1

HCID 230099053-[2-(Morpholin-4-yl)ethoxy]benzoic acid

Procedure

To the material of ethyl 3-{[2-(4-morpholinyl)ethyl]oxy}benzoate D47 (98 mg) was added HCl (0.5 mL, 16.46 mmol) at room temperature. The reaction was stirred at 100° for 2.5 hours. The mixture was concentrated in vacuo. To the residue was added 2 ml of ether and stirred for 0.5 hours, filtered. The filtrate was evaporated in vacuo to give the expected product D51 in 90 mg, as a white solid. LCMS Retention time=0.84 mins, [M+H]+ 252 (5 min run)

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionTo the residue was added 2 ml of ether
  3. stirringstirred for 0.5 hours
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-7c03c471a6314b659d13ef3203e41f47
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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