Benzaldehyde → N-{4-[trans-2-(benzylamino)cyclopropyl]phenyl}-3-(piperidin-1-yl)benzamide

HRID 922516ノート

反応式

HRID 922516 の反応式
Cl.Cl.[NH2:3][C@@H:4]1[CH2:6][C@H:5]1[C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:27])[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[CH:16]=2)=[CH:9][CH:8]=1.[CH:28](=O)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(=O)([O-])O.[Na+].[BH4-].[Na+]>CO.O>[CH2:28]([NH:3][C@@H:4]1[CH2:6][C@H:5]1[C:7]1[CH:8]=[CH:9][C:10]([NH:13][C:14](=[O:27])[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[CH:16]=2)=[CH:11][CH:12]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

参加物

7

反応物 4

HCID 240BenzaldehydeHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 86729856N-{4-[trans-2-aminocyclopropyl]phenyl}-3-(piperidin-1-yl)benzamide dihydrochloride

生成物 1

HCID 86729860N-{4-[trans-2-(benzylamino)cyclopropyl]phenyl}-3-(piperidin-1-yl)benzamide

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

To a solution of N-{4-[trans-2-aminocyclopropyl]phenyl}-3-(piperidin-1-yl)benzamide dihydrochloride (64.2 mg) in methanol (2 mL) were added benzaldehyde (16 μL) and sodium hydrogen carbonate (19.8 mg). The reaction mixture was stirred at 70° C. for 1 hr, and ice-cooled to 0° C. and sodium borohydride (8.9 mg) was added. The mixture was stirred for 1 hr and water was added. The mixture was extracted with ethyl acetate, and the extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (51.0 mg).

後処理

  1. temperatureice-cooled to 0° C.
  2. stirringThe mixture was stirred for 1 hr
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-045a5fd08c844fa8a3e6b38b97e95fb9
出典データセット
uspto-grants-2016_03
特許番号
US09278931B2

反応ノート

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