Stannous chloride dihydrate → 2,5-Dimorpholinopyridin-3-amine

HRID 1431380Notes

Reaction equation

HRID 1431380 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[C:9]([N+:19]([O-])=O)[C:10]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[N:11][CH:12]=2)[CH2:3][CH2:2]1.O.O.[Sn](Cl)Cl>CCOC(C)=O>[O:16]1[CH2:17][CH2:18][N:13]([C:10]2[C:9]([NH2:19])=[CH:8][C:7]([N:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)=[CH:12][N:11]=2)[CH2:14][CH2:15]1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 596312774-(5-Morpholino-3-nitropyridin-2-yl)morpholine

Product 1

HCID 596310462,5-Dimorpholinopyridin-3-amine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of 4-(5-morpholino-3-nitropyridin-2-yl)morpholine (1.22 g, 4.15 mmol; described herein) and EtOAc (50 mL) was added tin(II) chloride dihydrate (4.52 g, 20.7 mmol). The mixture was stirred at rt for ten min, refluxed for 2 h, and then cooled to rt. A solid was removed by filtration and both this and the EtOAc solution were washed with water and brine. The combined aq. portions were basified with 1M NaOH and the product extracted with EtOAc, dried (magnesium sulfate), and concentrated, affording 2,5-dimorpholinopyridin-3-amine as a beige solid. Mass Spectrum (ESI) m/e=265.2 (M+1).

Workup

  1. temperaturerefluxed for 2 h
  2. temperaturecooled to rt
  3. customA solid was removed by filtration
  4. washboth this and the EtOAc solution were washed with water and brine
  5. extractionthe product extracted with EtOAc
  6. dry with materialdried (magnesium sulfate)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-516f140b145f4443ae1f13c87e1c22fa
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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