Sodium Bicarbonate → HCID 58155241, compound

HRID 1929475Notes

Reaction equation

HRID 1929475 reaction equation
C(=[N:14][C:15]1[CH:16]=[CH:17][C:18]([F:31])=[C:19]([C:21]2([CH:28]3[CH2:30][CH2:29]3)[NH:26][C:25](=[S:27])[CH2:24][O:23][CH2:22]2)[CH:20]=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(=O)([O-])O.[Na+]>O1CCOCC1.Cl>[NH2:14][C:15]1[CH:16]=[CH:17][C:18]([F:31])=[C:19]([C:21]2([CH:28]3[CH2:29][CH2:30]3)[NH:26][C:25](=[S:27])[CH2:24][O:23][CH2:22]2)[CH:20]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 58155199HCID 58155199, compound

Product 1

HCID 58155241HCID 58155241, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of (RS)-5-[5-(benzhydrylidene-amino)-2-fluoro-phenyl]-5-cyclopropyl-morpholine-3-thione (1.42 g, 3.3 mmol) in dioxane (15 ml) and 1 M HCl (5 ml) was stirred at room temperature for 30 minutes. The reaction mixture was poured on a saturated solution of sodium hydrogen-carbonate and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated at reduced pressure. The residue was purified by chromatography on silica gel using a 3:1-mixture of dichloromethane and ethyl acetate as the eluent. CH2Cl2/EtOAc 3:1. The (RS)-5-(5-amino-2-fluoro-phenyl)-5-cyclopropyl-morpholine-3-thione was obtained as a white solid (0.810 g, 92% of theory). Mass (calculated) C13H15FN2OS [266.338]; (found) [M+H]+=267.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated at reduced pressure
  6. customThe residue was purified by chromatography on silica gel using a 3

Sources & evidence

ORD record
ord-95f0001178d5437c83dc82f98718dd73
Source dataset
uspto-grants-2012_05
Patent number
US08188079B2

Reaction notes

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