Benzyl Bromide → HCID 42645471、化合物

HRID 38254ノート

反応式

HRID 38254 の反応式
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:9][C:10]1[CH:11]=[C:12]([NH:22][C:23](=[O:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)[CH:13]=[CH:14][C:15]=1[N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH2:2]([N:19]1[CH2:20][CH2:21][N:16]([C:15]2[CH:14]=[CH:13][C:12]([NH:22][C:23](=[O:30])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[CH:11][C:10]=2[Cl:9])[CH2:17][CH2:18]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 67441344N-(3-chloro-4-(piperazin-1-yl)phenyl)picolinamide

生成物 1

HCID 42645471HCID 42645471、化合物収率 192.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

According to Scheme 5 Step 5 Method B: A suspension of (bromomethyl)benzene (0.61 mmol, 74 μL), N-(3-chloro-4-(piperazin-1-yl)phenyl)picolinamide (0.51 mmol, 161 mg) and of K2CO3 (0.51 mmol, 70 mg) in ACN (3 mL) was stirred at 80° C. for 30 minutes. After evaporation of the solvent, water and AcOEt were added. The aqueous phase was extracted with AcOEt. The organic phase was washed with brine, was dried over Na2SO4, was filtered and was concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel using DCM/AcOEt (80:20) as eluent and finally crystallized in pentane to obtain N-(4-(4-benzylpiperazin-1-yl)-3-chlorophenyl)picolinamide (0.98 mmol, 40 mg, 20%) as a white solid.

後処理

  1. customAfter evaporation of the solvent, water and AcOEt
  2. additionwere added
  3. extractionThe aqueous phase was extracted with AcOEt
  4. washThe organic phase was washed with brine
  5. dry with materialwas dried over Na2SO4
  6. filtrationwas filtered
  7. concentrationwas concentrated under reduced pressure
  8. customThe crude product was purified by flash chromatography over silica gel
  9. customfinally crystallized in pentane

出典と根拠

ORDレコード
ord-ffabc75a608944ac845f7dfd6409fe52
出典データセット
uspto-grants-2013_09
特許番号
US08524726B2

反応ノート

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