Dibenamine hydrochloride → 6-(2-Dibenzylamino-ethoxy)-1-ethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 2-dibenzylamino-ethyl ester

HRID 2099120

反応式

HRID 2099120 の反応式
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([OH:13])=[CH:10][CH:11]=2)[C:6](=[O:14])[C:5]([C:15]([OH:17])=[O:16])=[CH:4]1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl.[CH2:25]([N:32]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:33][CH2:34]Cl)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C>[CH2:25]([N:32]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:33][CH2:34][O:16][C:15]([C:5]1[C:6](=[O:14])[C:7]2[C:12](=[CH:11][CH:10]=[C:9]([O:13][CH2:34][CH2:33][N:32]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH:8]=2)[N:3]([CH2:1][CH3:2])[CH:4]=1)=[O:17])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

参加物

5

反応物 3

HCID 5925Dibenamine hydrochlorideHCID 11430Potassium CarbonateHCID 205700801-Ethyl-6-hydroxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

生成物 1

HCID 688611766-(2-Dibenzylamino-ethoxy)-1-ethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 2-dibenzylamino-ethyl ester収率 120.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
65 °C

実験手順

1-Ethyl-6-hydroxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (GB 1433774) (1.4 g, 6 mmol) was dissolved in dry DMF (80 mL). To this was added potassium carbonate (5 g, 36 mmol) and dibenzyl-(2-chloroethyl)amine hydrochloride (4.37 g, 14.8 mmol). The mixture was heated at 65° C. with stirring for 72 h, then allowed to cool overnight. The mixture was evaporated to a small volume, diluted with water and extracted with ethyl acetate (×2). The combined organic extracts were washed with brine, dried and evaporated under reduced pressure to give a dark viscous oil (4.9 g). This residue was purified by chromatography on silica gel (100 g), eluting with 0.2-3.8% methanol in dichloromethane, to give the title compound as a brown solid (2.46 g, 60%); ESMS m/z 680 [M+H]+ (100%).

後処理

  1. temperatureto cool overnight
  2. customThe mixture was evaporated to a small volume
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate (×2)
  5. washThe combined organic extracts were washed with brine
  6. customdried
  7. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-e36cd2b3b96745c3a9ab17171457347b
出典データセット
uspto-grants-2009_08
特許番号
US07569550B2

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