Desipramine → 3-{[3-(10,11-dihydro-dibenzo[b,f]azepine-5-yl)-propyl]-methyl-amino}-propionic Acid Ethyl Ester

HRID 840509

반응식

HRID 840509 반응식
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][N:6]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH2:14][CH2:13][C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]1=2.[CH2:21]([O:23][C:24](=[O:28])[CH2:25][CH2:26]Br)[CH3:22].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O.C1OCCOCCOCCOCCOCCOC1.CN(C=O)C>[CH2:21]([O:23][C:24](=[O:28])[CH2:25][CH2:26][N:2]([CH2:3][CH2:4][CH2:5][N:6]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=2[CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]1=2)[CH3:1])[CH3:22]

참가 물질

8

반응물 4

HCID 2995DesipramineHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 68320Ethyl 3-bromopropionate

생성물 1

HCID 691417273-{[3-(10,11-dihydro-dibenzo[b,f]azepine-5-yl)-propyl]-methyl-amino}-propionic Acid Ethyl Ester수율 89%

시약·촉매·용매 3

HCID 2855718-Crown-6촉매HCID 180Acetone용매HCID 6228Dimethylformamide용매

실험 절차

A solution of 6.02 g (19.8 mmol) of desipramine hydrochloride was allowed to stir at room temperature for 5 minutes. This was extracted with 6×100 ml of chloroform. The combined organic part was washed with 100 ml of water, dried with anhydrous Na2SO4 and concentrated to give 5.25 g of desipramine free base. A solution of 2.82 g (10.6 mmol) of desipramine free base in 100 ml of anhydrous acetone was added. To this reaction mixture 2.03 ml (15.8 mmol) of ethyl-3-bromopropionate, 3.65 g (26.4 mmol) of anhydrous potassium carbonate, 264 mg (1.76 mmol) of sodium iodide, 5 mg of 18-crown-6 and 0.7 ml of anhydrous DMF were added. The reaction mixture was allowed to reflux under argon overnight. The mixture was filtered and the residue was washed with 20 ml of acetone. The combined filtrate was concentrated and purified by silica gel column chromatography using 4% methanol in ethyl acetate to give 3.45 g (9.41 mmol, 89%) of the ethyl ester (17) as a thick oil.

후처리

  1. temperatureto reflux under argon overnight
  2. filtrationThe mixture was filtered
  3. washthe residue was washed with 20 ml of acetone
  4. concentrationThe combined filtrate was concentrated
  5. custompurified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-4a2d670f8ff74230a476fa42fde86bb6
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06368814B1

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