Hydrochloric Acid → 2-(Propan-2-yl)morpholine

HRID 737108Notes

Reaction equation

HRID 737108 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH:14]([CH3:16])[CH3:15])[CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[CH:14]([CH:10]1[O:11][CH2:12][CH2:13][NH:8][CH2:9]1)([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57849505HCID 57849505, compound

Product 1

HCID 198776882-(Propan-2-yl)morpholine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The above compound could be made in the following manner: 2-Isopropyl-morpholine-4-carboxylic acid tert-butyl ester in 4N solution of hydrogen chloride in dioxane could be stirred at 60° C. for 3 h. The solvent could be removed in vacuo and 1N aqueous hydrogen chloride solution could be added to the resulting residue, and the mixture could be washed with diethyl ether. The aqueous layer could be adjusted to pH 14 by addition of 2N NaOH solution and extracted with methylene chloride. The organic layer could be washed with brine and dried over sodium sulfate. After filtering, the material could be purified by column chromatography.

Workup

  1. customThe solvent could be removed in vacuo and 1N aqueous hydrogen chloride solution
  2. additioncould be added to the resulting residue
  3. washthe mixture could be washed with diethyl ether
  4. additionThe aqueous layer could be adjusted to pH 14 by addition of 2N NaOH solution
  5. extractionextracted with methylene chloride
  6. washThe organic layer could be washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationAfter filtering
  9. customthe material could be purified by column chromatography

Sources & evidence

ORD record
ord-afa4af7f1e1c4be7a55aee4bbb368bba
Source dataset
uspto-grants-2009_09
Patent number
US07595397B2

Reaction notes

Loading…