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

반응식

HRID 2099122 반응식
[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

참가 물질

5

반응물 3

HCID 5925Dibenamine hydrochloride2회HCID 11430Potassium Carbonate2회HCID 214453649-Hydroxy-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid

생성물 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 ester수율 89%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-5b3f986604304e2ea9dde706c43d7720
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07569550B2

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