Hydrogen chloride-ethyl acetate → 4-bromo-N-[(3R,4R)-3-(3,4-dichlorophenyl)piperidin-4-yl]-N-methylbenzamide

HRID 1260986노트

반응식

HRID 1260986 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]([CH3:32])[C@@H:11]2[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][C@H:12]2[C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([Cl:31])[CH:25]=2)=[O:9])=[CH:4][CH:3]=1.Cl.C(OCC)(=O)C>C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:10]([C@@H:11]2[CH2:16][CH2:15][NH:14][CH2:13][C@H:12]2[C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([Cl:31])[CH:25]=2)[CH3:32])=[O:9])=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86631417tert-butyl (3R,4R)-4-{[(4-bromophenyl)carbonyl](methyl)amino}-3-(3,4-dichlorophenyl)piperidine-1-carboxylate

생성물 1

HCID 689301054-bromo-N-[(3R,4R)-3-(3,4-dichlorophenyl)piperidin-4-yl]-N-methylbenzamide수율 93.4%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
50 °C

실험 절차

To a solution of the compound (1.09 g) obtained in step 2 in ethyl acetate (8 mL) was added 4N hydrogen chloride/ethyl acetate (8 mL), and the mixture was stirred at 50° C. for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in a mixture of ethyl acetate and acetonitrile. This solution was washed with 1N aqueous sodium hydroxide solution and dried, and the solvent was evaporated under reduced pressure to give 4-bromo-N-[(3R,4R)-3-(3,4-dichlorophenyl)piperidin-4-yl]-N-methylbenzamide (0.830 g, 93%) as a white powder.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in a mixture of ethyl acetate and acetonitrile
  3. washThis solution was washed with 1N aqueous sodium hydroxide solution
  4. customdried
  5. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-512c961a56e64d92a63ed61a9a98188a
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08470816B2

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