Acetic Acid → HCID 59507477, compound

HRID 1043778Notes

Reaction equation

HRID 1043778 reaction equation
C(O)(=O)C.[N+:5]([C:8]1[CH:9]=[CH:10][C:11]([O:14][CH:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[N:12][CH:13]=1)([O-:7])=[O:6].[CH3:21][C:22]([CH3:24])=O.C([BH3-])#N.[Na+]>CO>[CH:22]([N:18]1[CH2:19][CH2:20][CH:15]([O:14][C:11]2[CH:10]=[CH:9][C:8]([N+:5]([O-:7])=[O:6])=[CH:13][N:12]=2)[CH2:16][CH2:17]1)([CH3:24])[CH3:21]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5003444Sodium cyanoborohydrideHCID 45786952HCID 45786952, compound

Product 1

HCID 59507477HCID 59507477, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 10% acetic acid in methanol was added 5-nitro-2-(piperidin-4-yloxy)pyridine (1 eq) and anhydrous acetone (5 eq). The solution was stirred at room temperature for 1 hour. The reaction mixture was cooled to 0° C. on an ice bath and sodium cyanoborohydride (1.5 eq) was added. The reaction mixture was then warmed to room temperature and stirred for 5 hours. The solvent was evaporated, the residue brought to pH=10 with sodium carbonate and extracted with EtOAc. The organic layer was washed with water, brine, dried over sodium sulfate, and evaporated to give the crude material. Purification by silica gel column chromatography using 2% methanol/dichloromethane afforded the product as a yellow solid. LC/MS (m/z): 266.3 (MH+), Rt 1.85 minutes.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C. on an ice bath
  2. temperatureThe reaction mixture was then warmed to room temperature
  3. stirringstirred for 5 hours
  4. customThe solvent was evaporated
  5. extractionextracted with EtOAc
  6. washThe organic layer was washed with water, brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customto give the crude material
  10. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-da4c2b54a902400c80921a052e2c26cb
Source dataset
uspto-grants-2013_10
Patent number
US08563549B2

Reaction notes

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