4-Ethylbenzaldehyde → 1-(2-(4-(4-ethylbenzylamino)piperidin-1-yl)ethyl)-7-fluoroquinoxalin-2(1H)-one

HRID 39956

反応式

HRID 39956 の反応式
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([F:20])[CH:18]=3)[N:13]=[CH:12][C:11]2=[O:21])[CH2:4][CH2:3]1.[CH2:22]([C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1)[CH3:23].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(O)(=O)C.C(Cl)(Cl)Cl>[CH2:22]([C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH:1][CH:2]2[CH2:3][CH2:4][N:5]([CH2:8][CH2:9][N:10]3[C:19]4[C:14](=[CH:15][CH:16]=[C:17]([F:20])[CH:18]=4)[N:13]=[CH:12][C:11]3=[O:21])[CH2:6][CH2:7]2)=[CH:26][CH:25]=1)[CH3:23]

参加物

7

反応物 4

HCID 208614-EthylbenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 593979071-(2-(4-aminopiperidin-1-yl)ethyl)-7-fluoroquinoxalin-2(1H)-one

生成物 1

HCID 593982381-(2-(4-(4-ethylbenzylamino)piperidin-1-yl)ethyl)-7-fluoroquinoxalin-2(1H)-one

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6212Chloroform溶媒

実験手順

To 5 mL of a chloroform solution containing 301 mg of 1-(2-(4-aminopiperidin-1-yl)ethyl)-7-fluoroquinoxalin-2(1H)-one and 143 mg of 4-ethylbenzaldehyde, 60 μL of acetic acid were added, and stirred at room temperature for 1 hour. To the reaction mixture, 352 mg of sodium triacetoxyborohydride was added, and stirred for 1.5 hours. Aqueous saturated sodium hydrogen carbonate solution was added, the organic layer was separated. The organic layer was washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [Silica Gel; Fuji Silysia Chemical Ltd., Chromatorex-NH, eluent; ethyl acetate:hexane=1:1], to give 1-(2-(4-(4-ethylbenzylamino)piperidin-1-yl)ethyl)-7-fluoroquinoxalin-2(1H)-one as pale yellow solid.

後処理

  1. additionwere added
  2. stirringstirred for 1.5 hours
  3. customthe organic layer was separated
  4. washThe organic layer was washed with aqueous saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by silica gel column chromatography [Silica Gel; Fuji Silysia Chemical Ltd., Chromatorex-NH, eluent; ethyl acetate:hexane=1:1]

出典と根拠

ORDレコード
ord-759d40a4bf4a4131b388834e750b4488
出典データセット
uspto-grants-2013_09
特許番号
US08524738B2

関連ノート

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