Formaldehyde → 3,5-dimethoxy-N-{[4-(2-pyridinyl)-1-piperazinyl]methyl}benzamide

HRID 490185노트

반응식

HRID 490185 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.C=O.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([O:26][CH3:27])[CH:25]=1)[C:20]([NH2:22])=[O:21].[C:28](=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:27][O:26][C:24]1[CH:23]=[C:19]([CH:18]=[C:17]([O:16][CH3:15])[CH:25]=1)[C:20]([NH:22][CH2:28][N:10]1[CH2:9][CH2:8][N:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH2:12][CH2:11]1)=[O:21]

참가 물질

6

반응물 4

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 728783,5-DimethoxybenzamideHCID 944591-(2-Pyridyl)piperazine

생성물 1

HCID 104283533,5-dimethoxy-N-{[4-(2-pyridinyl)-1-piperazinyl]methyl}benzamide수율 108%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 1-pyridin-2-ylpiperazine (16 mg, 0.1 mmol, Aldrich), paraformaldehyde (30 mg, 1 mmol), 3,5-dimethoxybenzamide (91 mg, 0.5 mmol, Lancaster), and 42 mg of potassium carbonate (0.3 mmol) in 2 mL absolute ethyl alcohol was heated to reflux under nitrogen overnight. The mixture was cooled to room temperature, filtered, and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel (10% methanol:ethyl acetate) to give 38.5 mg (72%) pure compound. 1H NMR (500 MHz, DMSO-d6) δ 2.59 (t, J=4 Hz, 4H), 3.48 (t, J=4 Hz, 4H), 3.78 (s, 6H), 4.20 (d, J=5 Hz, 1H), 6.62 (m, 2H), 6.81 (d, J=6 Hz, 1H), 7.03 (s, 2H), 7.50 (t, J=6 Hz, 1H), 8.10 (d, J=5 Hz, 1H), 8.78 (t, J=5 Hz, 1H); MS (ESI/APCI−) m/e 355 (M−H)+.

후처리

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen overnight
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica gel (10% methanol:ethyl acetate)

출처 및 근거

ORD 기록
ord-5c50397a3a4c428c9855a1345a025889
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528134B2

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