Dibenamine hydrochloride → 9-(2-Dibenzylamino-ethoxy)-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid 2-dibenzylamino-ethyl ester

HRID 2099122

反応式

HRID 2099122 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:9]3=[C:10]([CH2:12][CH2:13][CH2:14][N:8]3[CH:7]=[C:6]([C:15]([OH:17])=[O:16])[C:5]2=[O:18])[CH:11]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[CH2:26]([N:33]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:34][CH2:35]Cl)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C>[CH2:26]([N:33]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:34][CH2:35][O:16][C:15]([C:6]1[C:5](=[O:18])[C:4]2[C:9]3=[C:10]([CH2:12][CH2:13][CH2:14][N:8]3[CH:7]=1)[CH:11]=[C:2]([O:1][CH2:35][CH2:34][N:33]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH:3]=2)=[O:17])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

参加物

5

反応物 3

HCID 5925Dibenamine hydrochloride2 回HCID 11430Potassium Carbonate2 回HCID 214453649-Hydroxy-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid

生成物 1

HCID 688610139-(2-Dibenzylamino-ethoxy)-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid 2-dibenzylamino-ethyl ester収率 89%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

9-Hydroxy-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid (GB1417129) (0.905 g, 3.69 mmol) was suspended in dry DMF (50 mL). To this was added potassium carbonate (3.06 g, 22 mmol) and dibenzyl-(2-chloroethyl)amine hydrochloride (2.37 g, 8 mmol). The mixture was heated at 60° C. for 16 h, then more potassium carbonate (0.55 g) and dibenzyl-(2-chloroethyl)amine hydrochloride (1.18 g, 4 mmol) were added. After a further 25 h at 75° C. the mixture was evaporated. The residue was diluted with water and extracted with ethyl acetate (×3). The combined organic extracts were washed with brine, dried and evaporated under reduced pressure. The crude product (4.0 g) was purified by chromatography on silica gel (100 g), eluting with 0-4% methanol in dichloromethane, to give the title compound (2.25 g, 89%); ESMS m/z 692 [M+H]+ (100%).

後処理

  1. customAfter a further 25 h at 75° C. the mixture was evaporated
  2. additionThe residue was diluted with water
  3. extractionextracted with ethyl acetate (×3)
  4. washThe combined organic extracts were washed with brine
  5. customdried
  6. customevaporated under reduced pressure
  7. customThe crude product (4.0 g) was purified by chromatography on silica gel (100 g)
  8. washeluting with 0-4% methanol in dichloromethane

出典と根拠

ORDレコード
ord-5b3f986604304e2ea9dde706c43d7720
出典データセット
uspto-grants-2009_08
特許番号
US07569550B2

関連ノート

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