Tetrahydrofuran → HCID 178526691, compound

HRID 22941

Reaction equation

HRID 22941 reaction equation
O1CCCC1.[NH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9][CH2:8]1.C(N(CC)CC)C.Cl[C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][N:23]=1>O>[N+:28]([C:25]1[CH:26]=[CH:27][C:22]([NH:6][C@H:7]2[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9][CH2:8]2)=[N:23][CH:24]=1)([O-:30])=[O:29]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 783082-Chloro-5-nitropyridineHCID 178511715HCID 178511715, compound

Product 1

HCID 178526691HCID 178526691, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 150 ml of a tetrahydrofuran suspension containing 10 g of trans-4-aminocyclohexanol was added 15ml of triethylamine, 50 ml of a tetrahydrofuran solution containing 2-chloro-5-nitropyridine was further added thereto under ice-cooling, and then, the mixture was stirred at room temperature for 18 hours. Water was added to the reaction mixture and the mixture was extracted with chloroform. The extract was washed with brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel flash column chromatography (solvent: ethyl acetate-hexane (2:1)) to obtain 8.52 g of trans-4-(5-nitro-2-pyridylamino)cyclohexanol.

Workup

  1. additionwas further added
  2. temperatureunder ice-cooling
  3. extractionthe mixture was extracted with chloroform
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by silica gel flash column chromatography (solvent: ethyl acetate-hexane (2:1))

Sources & evidence

ORD record
ord-bacd710fc5fe481bbf029ea3a08e93f4
Source dataset
uspto-grants-2005_02
Patent number
US06849622B2

Linked notes

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