Tetrahydrofuran → 4-(3-Bromo-5-nitropyridin-2-yl)morpholine

HRID 2406714Notes

Reaction equation

HRID 2406714 reaction equation
C(N(CC)CC)C.[NH:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.O1CCCC1.[Br:19][C:20]1[C:21](Cl)=[N:22][CH:23]=[C:24]([N+:26]([O-:28])=[O:27])[CH:25]=1>O>[Br:19][C:20]1[C:21]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:22][CH:23]=[C:24]([N+:26]([O-:28])=[O:27])[CH:25]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8083MorpholineHCID 8471TriethylamineHCID 2308893-Bromo-2-chloro-5-nitropyridine

Product 1

HCID 467388804-(3-Bromo-5-nitropyridin-2-yl)morpholineYield 95.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Triethylamine (191 mg) and morpholine (120 mg) were added to a tetrahydrofuran (4 ml) solution containing 3-bromo-2-chloro-5-nitropyridine (300 mg), followed by stirring for 40 minutes. Water was added to the reaction solution, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate. Subsequently, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (chloroform:methanol=1:0 to 3:1), and a yellow solid of 4-(3-bromo-5-nitropyridin-2-yl)morpholine (346 mg) was thus obtained.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe resultant was washed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationSubsequently, the solvent was distilled away under reduced pressure
  5. customthe obtained residue was purified by silica gel chromatography (chloroform:methanol=1:0 to 3:1)

Sources & evidence

ORD record
ord-cae4fa630e6f466b8d9745dd238dabe9
Source dataset
uspto-grants-2014_08
Patent number
US08809371B2

Reaction notes

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