Hydrochloric Acid → HCID 23587792, compound

HRID 489287Notes

Reaction equation

HRID 489287 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:15]([OH:17])=O)[C:6]1=[O:18])[CH2:2][CH2:3][CH3:4].S(Cl)(Cl)=O.[CH2:23]([NH2:31])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.Cl>C1(C)C=CC=CC=1.CN(C=O)C>[CH2:23]([NH:31][C:15]([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)=[O:17])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1001PhenethylamineHCID 24386Thionyl ChlorideHCID 22266516HCID 22266516, compound

Product 1

HCID 23587792HCID 23587792, compoundYield 74.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

1-Butyl-2-oxo-1,2,5,6,7,8-hexahydroquinoline-3-carboxylic acid (4-002-01) (100 mg, 0.38 mmol) was dissloved in toluene (10 mL), and to the reaction mixture were added thionyl chloride (83 μL, 1.14 mmol) and catalytic amount of DMF, and the reaction mixture was reacted at 75° C. for 30 min. The reaction mixture was evaporated under reduced pressure and the residue was dissolved in methylene chloride (5 mL). To the reaction mixture was added phenethylamine (143 μL, 1.14 mmol) and the reaction mixture was stirred at room temperature for 10 min. To the reaction mixture was added diluted hydrochloric acid (1 mol/L, 10 mL) and the reaction mixture was extracted with ethyl acetate (30 mL), washed with brine (10 mL), dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (toluene/ethyl acetate), followed by recrystallization from diethyl ether to give 1-butyl-2-oxo-1,2,5,6,7,8-hexahydroquinoline-3-carboxylic acid phenethylamide (4-002) (100 mg, 74%) as white crystal.

Workup

  1. customthe reaction mixture was reacted at 75° C. for 30 min
  2. customThe reaction mixture was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in methylene chloride (5 mL)
  4. extractionthe reaction mixture was extracted with ethyl acetate (30 mL)
  5. washwashed with brine (10 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (toluene/ethyl acetate)
  9. customfollowed by recrystallization from diethyl ether

Sources & evidence

ORD record
ord-4ea82e1471904a76880db0372eb0e6c1
Source dataset
uspto-grants-2005_12
Patent number
US06977266B2

Reaction notes

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