Hydrochloric Acid → (E)-4-morpholinobut-2-enoic acid

HRID 2284650Notes

Reaction equation

HRID 2284650 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7]/[CH:8]=[CH:9]/[C:10]([O:12]C(C)(C)C)=[O:11])[CH2:3][CH2:2]1.Cl>C1(C)C=CC=CC=1>[O:1]1[CH2:2][CH2:3][N:4]([CH2:7]/[CH:8]=[CH:9]/[C:10]([OH:12])=[O:11])[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90051723(E)-tert-butyl 4-morpholino-2-butenoate

Product 1

HCID 22466617(E)-4-morpholinobut-2-enoic acidYield 99.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To (E)-tert-butyl 4-morpholino-2-butenoate (B14, 179 mg), 1.0 mol/L aqueous hydrochloric acid (4 mL) was added at room temperature, and the mixture was stirred for 1 hour and 40 minutes under reflux by heating. The reaction mixture was cooled to room temperature, and then toluene was added to the mixture, and the solvent was evaporated under reduced pressure. To the obtained residue, ethyl acetate was added. The solid matter was taken by filtration, washed with chloroform, and then dried under reduced pressure to obtain (E)-4-morpholino-2-butenoic acid (B15) hydrochloride (134 mg).

Workup

  1. temperatureunder reflux
  2. temperatureby heating
  3. customthe solvent was evaporated under reduced pressure
  4. additionTo the obtained residue, ethyl acetate was added
  5. filtrationThe solid matter was taken by filtration
  6. washwashed with chloroform
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-67bf9a846e2f486db25dedb5394d1ee6
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

Loading…