Hydrochloric Acid → 2-Butyl-3-oxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carboxylic acid benzylamide

HRID 416581Notes

Reaction equation

HRID 416581 reaction equation
[CH2:1]([N:5]1[C:14](=[O:15])[C:13]([C:16]([OH:18])=O)=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][CH2:11]2)=[CH:6]1)[CH2:2][CH2:3][CH3:4].S(Cl)(Cl)=O.[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl>C1(C)C=CC=CC=1.C(Cl)Cl.CN(C=O)C>[CH2:23]([NH:30][C:16]([C:13]1[C:14](=[O:15])[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH:6]=[C:7]2[C:12]=1[CH2:11][CH2:10][CH2:9][CH2:8]2)=[O:18])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 24386Thionyl ChlorideHCID 222665212-Butyl-3-oxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carboxylic acid

Product 1

HCID 235880372-Butyl-3-oxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carboxylic acid benzylamideYield 74%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

2-Butyl-3-oxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carboxylic acid (4-501-05) (5 mg, 0.02 mmol) was dissolved in toluene (1 mL), and to the reaction mixture were added thionyl chloride (4.4 μL, 0.06 mmol) and catalytic amount of DMF, and the reaction mixture was reacted at 75° C. for 30 min. After concentration of the reaction mixture under reduced pressure, the residue was dissolved in methylene chloride (1 mL), and then benzylamine (6.2 μL, 0.06 mmol) was added to the reaction mixture, and the reaction mixture was stirred at room temperature for 10 min. To the reaction mixture was added diluted hydrochloric acid (1 mol/L, 3 mL), and the reaction mixture was extracted with ethyl acetate (8 mL), washed with brine (4 mL), dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (toluene/ethyl acetate) to give 2-butyl-3-oxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carboxylic acid benzylamide (4-501) (5 mg, 74%) as a white crystal.

Workup

  1. customthe reaction mixture was reacted at 75° C. for 30 min
  2. extractionthe reaction mixture was extracted with ethyl acetate (8 mL)
  3. washwashed with brine (4 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (toluene/ethyl acetate)

Sources & evidence

ORD record
ord-a3a194bf720d4ea88058e20c155a8ada
Source dataset
uspto-grants-2012_01
Patent number
US08088924B2

Reaction notes

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