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

HRID 490185

反応式

HRID 490185 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-5c50397a3a4c428c9855a1345a025889
出典データセット
uspto-grants-2009_05
特許番号
US07528134B2

関連ノート

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