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

HRID 2063349Notes

Reaction equation

HRID 2063349 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([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)[O:4][N:3]=1.[ClH:26]>C(OCC)(=O)C>[ClH:26].[CH3:1][C:2]1[N:6]=[C:5]([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)[O:4][N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58097887(2S)-tert-butyl 2-(4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)morpholine-4-carboxylate2×

Product 1

HCID 66842520(2S)-2-(4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)morpholine hydrochlorideYield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of (2S)-tert-butyl 2-(4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)morpholine-4-carboxylate (intermediate 18, 20.5 g, 59.4 mmol) in ethyl acetate (50 ml) was added hydrogen chloride (4N) in ethyl acetate (200 ml) at room temperature and stirred for 3 hours. The solvent was evaporated under reduced pressure, and the precipitate was filtered, washed with ethyl acetate and dried under reduced pressure to afford (2S)-2-(4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)morpholine hydrochloride (intermediate 19, 16.7 g, 99%).

Workup

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

Sources & evidence

ORD record
ord-b356cae3fc0143d4ad32484206715092
Source dataset
uspto-grants-2012_10
Patent number
US08288383B2

Reaction notes

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