Benzyl Alcohol → HCID 23587938, compound

HRID 416584Notes

Reaction equation

HRID 416584 reaction equation
[CH2:1]([N:5]1[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=[C:7](C(O)=O)[C:6]1=[O:18])[CH2:2][CH2:3][CH3:4].S(Cl)(Cl)=O.[N-]=[N+]=[N-].[Na+].[CH2:27]([OH:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C[N:36]([CH:38]=[O:39])C>C1(C)C=CC=CC=1.O>[CH2:27]([O:34][C:38](=[O:39])[NH:36][C:7]1[C:6](=[O:18])[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

8

Reactant 5

HCID 244Benzyl AlcoholHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 22266516HCID 22266516, compound

Product 1

HCID 23587938HCID 23587938, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

1-Butyl-2-oxo-1,2,5,6,7,8-hexahydroquinoline-3-carboxylic acid (4-002-01) (100 mg, 0.38 mmol) was dissolved in toluene (5 mL), and to the reaction mixture were added thionyl chloride (57 μL, 0.76 mmol) and catalytic amount of DMF, and the reaction mixture was reacted at 75° C. for 30 min. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in acetone (5 mL), and then to the reaction mixture was added an aqueous solution of sodium azide (29 mg, 0.42 mmol) (0.5 mL), and the reaction mixture was stirred at room temperature for 15 min. To the reaction mixture was added water (5 mL), the reaction mixture was extracted with ethyl acetate (10 mL), washed with brine (5 mL), dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The residue was dissolved in toluene (5 mL), and the reaction mixture was reacted at 120° C. for 30 min, and then benzyl alcohol (46 μL, 0.44 mmol) was added to the reaction mixture, and the reaction mixture was stirred at 120° C. for 2 h. The reaction mixture was purified by silica gel column chromatography (toluene/ethyl acetate), to give (1-butyl-2-oxo-1,2,5,6,7,8-hexahydroquinolin-3-yl)carbamic acid benzyl ester (6-007) (90 mg, 63%) as a white foamy substance.

Workup

  1. customthe reaction mixture was reacted at 75° C. for 30 min
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in acetone (5 mL)
  4. extractionthe reaction mixture was extracted with ethyl acetate (10 mL)
  5. washwashed with brine (5 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated under reduced pressure
  8. dissolutionThe residue was dissolved in toluene (5 mL)
  9. customthe reaction mixture was reacted at 120° C. for 30 min
  10. stirringthe reaction mixture was stirred at 120° C. for 2 h
  11. customThe reaction mixture was purified by silica gel column chromatography (toluene/ethyl acetate)

Sources & evidence

ORD record
ord-4d45a12ca15f4998a5ec24f25c477b98
Source dataset
uspto-grants-2012_01
Patent number
US08088924B2

Reaction notes

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