Dimethylamine, hydrochloride → N,N-Dimethyl-2-oxo-1,2,3,4-tetrahydro-3-quinolineacetoamide

HRID 2269713Notes

Reaction equation

HRID 2269713 reaction equation
[O:1]=[C:2]1[CH:11]([CH2:12][C:13]([OH:15])=O)[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.C[CH2:17][N:18]=[C:19]=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.CNC>C1COCC1.C(#N)C.O.C(N(CC)CC)C>[CH3:17][N:18]([CH3:19])[C:13](=[O:15])[CH2:12][CH:11]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3][C:2]1=[O:1]

Participants

9

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 183329702-(2-Oxo-1,2,3,4-tetrahydroquinolin-3-YL)acetic acid

Product 1

HCID 10585665N,N-Dimethyl-2-oxo-1,2,3,4-tetrahydro-3-quinolineacetoamideYield 67.6%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To the mixed solution of 2-oxo-1,2,3,4-tetrahydro-3-quinolineacetic acid (810 mg) in THF (10 ml) and acetonitrile (10 ml), WSC (1.15 g), HOBt (610 mg), dimethylamine hydrochloride (650 mg) and triethylamine (1.67 ml) were added subsequently, which was stirred at room temperature overnight. Water was added to the reaction mixture, which was extracted with a mixed solvent of ethyl acetate-THF (1:1). The organic layer was washed subsequently with 0.1N aqueous hydrochloric acid solution, a saturated aqueous sodium bicarbonate solution, and a saturated aqueous sodium chloride solution, then dried and concentrated to obtain the entitled compound (620 mg).

Workup

  1. extractionwas extracted with a mixed solvent of ethyl acetate-THF (1:1)
  2. washThe organic layer was washed subsequently with 0.1N aqueous hydrochloric acid solution
  3. dry with materiala saturated aqueous sodium bicarbonate solution, and a saturated aqueous sodium chloride solution, then dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-da3c7ded1c084ffcaa59d359b91b513d
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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