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

HRID 922520
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HRID 922520 반응식
Cl.[NH2:2][C@@H:3]1[CH2:5][C@H:4]1[C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:27])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][C:21]3=[O:26])[CH:15]=2)=[CH:8][CH:7]=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:2][C@@H:3]1[CH2:5][C@H:4]1[C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:27])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][C:21]3=[O:26])[CH:15]=2)=[CH:8][CH:7]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1
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참가 물질

7

반응물 4

HCID 240BenzaldehydeHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 86729861N-{4-[trans-2-aminocyclopropyl]phenyl}-3-(2-oxopiperidin-1-yl)benzamide hydrochloride

생성물 1

HCID 86729865N-{4-[trans-2-(benzylamino)cyclopropyl]phenyl}-3-(2-oxopiperidin-1-yl)benzamide

시약·촉매·용매 2

HCID 887
Methanol
용매
HCID 962Water용매

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온도
70 °C

실험 절차

To a solution of N-{4-[trans-2-aminocyclopropyl]phenyl}-3-(2-oxopiperidin-1-yl)benzamide hydrochloride (27.1 mg) in methanol (1 mL) were added benzaldehyde (7.14 μL) and sodium hydrogen carbonate (8.9 mg). The mixture was stirred at 70° C. for 1 hr, and ice-cooled to 0° C. and sodium borohydride (4.0 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 (10.9 mg).

후처리

  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)

출처 및 근거

ORD 기록
ord-d4e4ba6e30ab4d258f8f4afc6a16b464
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09278931B2

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