Piperidine → (4-Benzylamino-phenyl)-piperidin-1-yl-methanone

HRID 2380967노트

반응식

HRID 2380967 반응식
[CH2:1]([NH:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.Cl.C(N=C=NCCCN(C)C)C.O.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C>C(#N)C.O>[CH2:1]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:15])=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

8

반응물 5

HCID 8082PiperidineHCID 8471TriethylamineHCID 8535464-(Benzylamino)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178526939HCID 178526939, 화합물

생성물 1

HCID 67130556(4-Benzylamino-phenyl)-piperidin-1-yl-methanone

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

To a stirred suspension of 4-(benzylamino)benzoic acid (200 mg, 0.88 mmol) in acetonitrile (2 ml) was added piperidine (0.174 ml, 1.8 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (184 mg, 0.97 mmol), hydroxybenzotriazole hydrate (10 mg, catalytic) followed by triethylamine (0.31 ml, 2.2 mmol) and the reaction was stirred at room temperature for 16 hours. The reaction mixture was diluted with water (2 ml) and extracted with dichloromethane (2×2 ml). The organic phases were combined, washed with brine, dried over magnesium sulfate and then concentrated in vacuo. The residue was purified by flash column chromatography (SiO2) eluting with ethyl acetate/dichloromethane (1:4) to afford the title compound as an off white solid (122 mg, 47% yield).

후처리

  1. extractionextracted with dichloromethane (2×2 ml)
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography (SiO2)
  6. washeluting with ethyl acetate/dichloromethane (1:4)

출처 및 근거

ORD 기록
ord-478b7767e245437aa82144000540f4fc
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08258138B2

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