Hydrochloric Acid → 3-(Morpholin-4-yl)propanoic acid

HRID 634733Notes

Reaction equation

HRID 634733 reaction equation
[OH-].[K+].[O:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][C:11]([O:13]C)=[O:12])[CH2:5][CH2:4]1.Cl>C(O)C>[O:3]1[CH2:4][CH2:5][N:6]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 1013734-Morpholinepropanoic acid, methyl ester

Product 1

HCID 4108133-(Morpholin-4-yl)propanoic acidYield 109.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Potassium hydroxide (485 mg, 8.6mmol) was added to a solution of methyl 3-morpholinopropionate (1 g, 5.7 mmol) in ethanol (20 ml) and the mixture stirred for 2 hours at 80° C. The solution was allowed to cool and adjusted to pH1 with 6M hydrochloric acid. Insoluble material was removed by filtration and the volatiles removed from the filtrate by evaporation. The resulting oil was triturated with ether, the solid product collected by filtration, washed with methylene chloride and dried under vacuum to give 3-morpholinopropionic acid (993 mg, 89%) as a white solid.

Workup

  1. temperatureto cool
  2. customInsoluble material was removed by filtration
  3. customthe volatiles removed from the filtrate by evaporation
  4. customThe resulting oil was triturated with ether
  5. filtrationthe solid product collected by filtration
  6. washwashed with methylene chloride
  7. customdried under vacuum

Sources & evidence

ORD record
ord-86cdfda27d254be487ffcb57eed83c91
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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