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

HRID 2269713노트

반응식

HRID 2269713 반응식
[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]

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 962Water용매HCID 6342Acetonitrile용매HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-da3c7ded1c084ffcaa59d359b91b513d
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06329389B1

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