Hydrochloric Acid → (RS)-5-(3-amino-phenyl)-5-methyl-morpholin-3-one hydrochloride

HRID 1929459Notes

Reaction equation

HRID 1929459 reaction equation
C(=[N:14][C:15]1[CH:16]=[C:17]([C:21]2([CH3:28])[NH:26][C:25](=[O:27])[CH2:24][O:23][CH2:22]2)[CH:18]=[CH:19][CH:20]=1)(C1C=CC=CC=1)C1C=CC=CC=1.[ClH:29]>O1CCOCC1>[ClH:29].[NH2:14][C:15]1[CH:16]=[C:17]([C:21]2([CH3:28])[NH:26][C:25](=[O:27])[CH2:24][O:23][CH2:22]2)[CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58155203(RS)-5-[3-(benzhydrylidene-amino)-phenyl]-5-methyl-morpholin-3-one

Product 1

HCID 66931504(RS)-5-(3-amino-phenyl)-5-methyl-morpholin-3-one hydrochlorideYield 88%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of (RS)-5-[3-(benzhydrylidene-amino)-phenyl]-5-methyl-morpholin-3-one (5.62 g, 15 mmol) in dioxane (75 ml) was cooled to 15° C. and treated dropwise with 1 N hydrochloric acid (18 ml). The reaction mixture was stirred at room temperature overnight. For the workup, the reaction mixture was evaporated at reduced pressure, and the residue was portioned between diethylether (120 ml) and 1 N hydrochloric acid (20 ml). The aqueous phase was separated and washed with diethylether (120 ml). This procedure was repeated twice. The combined aqueous layers were evaporated at reduced pressure, and 3.27 g (88% of theory) of (RS)-5-(3-amino-phenyl)-5-methyl-morpholin-3-one hydrochloride were obtained as a yellowish solid used in the next step without further purification. Mass (calculated) C11H15ClN2O2 [242.707]; (found) [M+H]+=207.

Workup

  1. customFor the workup, the reaction mixture was evaporated at reduced pressure
  2. customThe aqueous phase was separated
  3. washwashed with diethylether (120 ml)
  4. customThe combined aqueous layers were evaporated at reduced pressure

Sources & evidence

ORD record
ord-ac155ce95c60482a82b9faff1c9adfc1
Source dataset
uspto-grants-2012_05
Patent number
US08188079B2

Reaction notes

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