Hydrochloric Acid → Ethyl morpholine-3-carboxylate

HRID 969263Notes

Reaction equation

HRID 969263 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH:2]1[C:7]([OH:9])=[O:8].Cl.[CH2:11](O)[CH3:12]>>[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH:2]1[C:7]([O:9][CH2:11][CH3:12])=[O:8]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 33401523-Morpholinecarboxylic acid

Product 1

HCID 18354446Ethyl morpholine-3-carboxylate

Procedure

A solution of morpholine-3-carboxylic acid (4.035 g; 30.8 mmol) in ethanol (250 ml) was saturated with gaseous HCl, then stirred for a week. The solvent was evaporated and the residue taken up in water and made basic (pH˜10) with sodium hydrogen carbonate and sodium carbonate. The mixture was then extracted with dichloromethane (7×), the combined extracts dried (Na2SO4) and the solvent evaporated to give ethyl morpholine-3-carboxylate (746 mg). EIMS: m/z=160.4 [M+H]+. This ester derivative and lithium aluminium hydride (1 M in THF, 9.4 ml, 9.4 mmol) were carefully combined under a nitrogen atmosphere and following addition were heated to reflux. After 5 h the reaction was cooled to room temperature and carefully quenched using dropwise water addition with ice cooling, then filtered and washed with dichloromethane. The solvent was evaporated to give 3-(hydroxymethyl)morpholine (409 mg). EIMS: m/z=118.2 (M+H)+.

Workup

  1. customThe solvent was evaporated
  2. extractionThe mixture was then extracted with dichloromethane (7×)
  3. dry with materialthe combined extracts dried (Na2SO4)
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-f5dff8749ff84db098657cf854940b0e
Source dataset
uspto-grants-2007_12
Patent number
US07307073B2

Reaction notes

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