Hydrochloric Acid → 4-(4-((5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl)phenyl)morpholin-3-one hydrochloride

HRID 1054156Notes

Reaction equation

HRID 1054156 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][C:14]3=[O:19])=[CH:9][CH:8]=2)[CH2:5][C@H:4]([CH2:20][N:21]2C(=O)C3C(=CC=CC=3)C2=O)[O:3]1.CN.[ClH:34]>CO>[ClH:34].[NH2:21][CH2:20][C@@H:4]1[O:3][C:2](=[O:1])[N:6]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][C:14]3=[O:19])=[CH:9][CH:8]=2)[CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 116903172-[[(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]isoindole-1,3-dione

Product 1

HCID 160370774-(4-((5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl)phenyl)morpholin-3-one hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
27.5 °C

Procedure

In a four neck round bottom flask, charged methanol (2900 ml), 2-([(5S)-2-Oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dione (290 g), and 40% aqueous methylamine (265 g) at 25 to 30° C. Reaction mass is stirred for 1 h at 25 to 30° C. and then heated to 60 to 65° C., and maintained at same temperature for 4 h. Reaction mixture then cooled to 25 to 30° C. and added conc. hydrochloric acid (290 ml, pH should be 1 to 2) and stirred for 30 minutes. Obtained solid is filtered off and washed by chilled methanol (290 ml).

Workup

  1. customReaction mass
  2. temperatureheated to 60 to 65° C.
  3. temperaturemaintained at same temperature for 4 h
  4. customReaction mixture
  5. temperaturethen cooled to 25 to 30° C.
  6. stirringstirred for 30 minutes
  7. customObtained solid
  8. filtrationis filtered off
  9. washwashed
  10. temperatureby chilled methanol (290 ml)

Sources & evidence

ORD record
ord-66111dddfbe54fe891af7aa26aacf3b7
Source dataset
uspto-grants-2016_07
Patent number
US09394292B2

Reaction notes

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