Hydrochloric Acid → (2S)-2-(4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl)morpholine hydrochloride

HRID 218321Notes

Reaction equation

HRID 218321 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([C@@H:13]3[O:18][CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]3)=[CH:9][CH:8]=2)[N:3]=1.[ClH:26]>C(OCC)(=O)C>[ClH:26].[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([C@@H:13]3[O:18][CH2:17][CH2:16][NH:15][CH2:14]3)=[CH:9][CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58121163tert-butyl (2S)-2-(4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl)morpholine-4-carboxylate2×

Product 1

HCID 66603801(2S)-2-(4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl)morpholine hydrochlorideYield 96%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of tert-butyl (2S)-2-(4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl) morpholine-4-carboxylate (intermediate 18, 16.9 g, 49.0 mmol) in ethyl acetate (60 ml) was added 4N hydrogen chloride in ethyl acetate (150 ml) at room temperature and the solution was stirred for 3 hours. The solvent was evaporated under reduced pressure, and the resulting precipitate was filtered, washed with ethyl acetate, and dried under reduced pressure to afford (2S)-2-(4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl)morpholine hydrochloride (intermediate 19, 13.3 g, 96%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. filtrationthe resulting precipitate was filtered
  3. washwashed with ethyl acetate
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-96c610a47c4c4d30bd7741a0177b6b67
Source dataset
uspto-grants-2012_06
Patent number
US08198437B2

Reaction notes

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