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

HRID 2269713ノート

反応式

HRID 2269713 の反応式
[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]

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-da3c7ded1c084ffcaa59d359b91b513d
出典データセット
uspto-grants-2001_12
特許番号
US06329389B1

反応ノート

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