Desipramine → {2-[3-(10,11-Dihydro-dibenzo[b,f]azepin-5-yl)-propylamino]-ethyl]-carbamic Acid tert-butyl Ester

HRID 840511

반응식

HRID 840511 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.C(=O)([O-])[O-].[K+].[K+].[C:27]([NH:34][CH2:35]CBr)([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].[I-].[Na+]>C1OCCOCCOCCOCCOCCOC1.CN(C)C=O.CC(C)=O>[C:30]([O:29][C:27](=[O:28])[NH:34][CH2:35][CH2:1][NH: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)([CH3:33])([CH3:32])[CH3:31]

참가 물질

8

반응물 4

HCID 2995DesipramineHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamate

생성물 1

HCID 86757926{2-[3-(10,11-Dihydro-dibenzo[b,f]azepin-5-yl)-propylamino]-ethyl]-carbamic Acid tert-butyl Ester수율 97.2%

시약·촉매·용매 3

HCID 2855718-Crown-6촉매HCID 180Acetone용매HCID 6228Dimethylformamide용매

실험 절차

To 3.23 g (12.04 mmol) of desipramine free base was added 80 ml of dry acetone, 3.6 g of anhydrous potassium carbonate, 3.0 g (13.45 mmol) of 2-(BOC-amino) ethyl bromide, 3 ml of anhydrous dimethylformamide, 15 mg of 18-crown-6 and 500 mg of sodium iodide. The mixture was allowed to reflux 18 hours under argon atmosphere. The reaction mixture was cooled to room temperature and filtered. The residue was washed with 10 ml of acetone. The filtrate was concentrated and the residue was purified by silica gel column chromatography using 4% methanol in ethyl acetate to give 4.8 g (11.7 mmol, 96%) of 23 as a thick oil.

후처리

  1. temperatureto reflux 18 hours under argon atmosphere
  2. filtrationfiltered
  3. washThe residue was washed with 10 ml of acetone
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-45a1cb867cff4c698d001297c3c0a26d
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06368814B1

연결된 노트

불러오는 중…