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

HRID 2294154
ノート
印刷プレビュー

反応式

HRID 2294154 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 887Methanol溶媒
HCID 962
Water
溶媒
HCID 6344Dichloromethane溶媒
HCID 11430Potassium Carbonate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d495feaf3efc471bb2cd5223249bbbe7
出典データセット
uspto-grants-1997_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05688795

反応ノート

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