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Hydrochloric Acid → 2-{3-[4-(4-bromo-2-methoxyphenyl)piperazin-1-yl]propylamino}-N,N-dimethylnicotinamide

HRID 2294154
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HRID 2294154 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH:18][C:19]2[N:29]=[CH:28][CH:27]=[CH:26][C:20]=2[C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[CH2:11][CH2:10]1.Cl.[Br:31]N1C(=O)CCC1=O>C(Cl)Cl.CO.O.C([O-])([O-])=O.[K+].[K+]>[Br:31][C:7]1[CH:6]=[CH:5][C:4]([N:9]2[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][NH:18][C:19]3[N:29]=[CH:28][CH:27]=[CH:26][C:20]=3[C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[CH2:13][CH2:14]2)=[C:3]([O:2][CH3:1])[CH:8]=1
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참가 물질

8

반응물 3

HCID 313Hydrochloric AcidHCID 67184N-bromobutanimideHCID 98655772-(3-(4-(2-Methoxyphenyl)piperazin-1-yl)propylamino)-N,N-dimethylnicotinamide

생성물 1

HCID 214734832-{3-[4-(4-bromo-2-methoxyphenyl)piperazin-1-yl]propylamino}-N,N-dimethylnicotinamide수율 75.5%

시약·촉매·용매 4

HCID 887Methanol용매
HCID 962
Water
용매
HCID 6344Dichloromethane용매
HCID 11430Potassium Carbonate용매

실험 절차

2-{3-[4-(2-Methoxyphenyl)piperazin-1-yl]propylamino}-N,N-dimethylnicotinamide (0.21 g, 0.53 mmol), prepared as in Example 21, was dissolved in methylene chloride and the solution was treated with excess hydrochloric acid in methanol and concentrated under reduced pressure. The residue was dissolved in 6 mL of DMF and N-bromosuccinimide (0.101 g, 0.57 mmol) was added. The mixture was stirred at room temperature for approximately 24 hours, diluted with water and basified with K2CO3. The basified mixture was extracted with ethyl acetate and the ethyl acetate layer was washed with brine, dried (MgSO4), filtered and concentrated. The residue was purified on silica gel by column chromatography eluting with 5% methanol/methylene chloride to give 2-{3-[4-(4-bromo-2-methoxyphenyl)piperazin-1-yl]propylamino}-N,N-dimethylnicotinamide (0.19 g, 0.40 mmol) as an oil.

후처리

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in 6 mL of DMF
  3. extractionThe basified mixture was extracted with ethyl acetate
  4. washthe ethyl acetate layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified on silica gel by column chromatography
  9. washeluting with 5% methanol/methylene chloride

출처 및 근거

ORD 기록
ord-d495feaf3efc471bb2cd5223249bbbe7
출처 데이터셋
uspto-grants-1997_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05688795

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