Formaldehyde → N-{[4-(2-pyridinyl)-1-piperazinyl]methyl}cyclohexanecarboxamide

HRID 490186

反応式

HRID 490186 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.[CH:15]1([C:21]([NH2:23])=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.[C:24](=O)([O-])[O-].[K+].[K+]>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:8][CH2:9][N:10]([CH2:24][NH:23][C:21]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:22])[CH2:11][CH2:12]1

参加物

6

反応物 4

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 14283CyclohexanecarboxamideHCID 944591-(2-Pyridyl)piperazine

生成物 1

HCID 10470197N-{[4-(2-pyridinyl)-1-piperazinyl]methyl}cyclohexanecarboxamide収率 99.2%

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), cyclohexanecarboxylic acid amide (64 mg, 0.5 mmol, Aldrich), 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 30 mg (66%) pure compound. 1H NMR (500 MHz, DMSO-d6) δ 1.05-1.40 (m, 5H), 1.59-1.68 (m, 5H), 2.15 (m, 1H), 2.48 (m, 4H), 3.45 (t, J=4 Hz, 4H), 3.95 (d, J=5 Hz, 1H), 6.62 (t, J=6 Hz, 1H), 6.81 (d, J=6 Hz, 1H), 7.53 (t, J=6 Hz, 1H), 8.01 (t, J=5 Hz, 1H), 8.10 (d, J=5 Hz, 1H); MS (ESI/APCI−) m/e 301 (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-7ff2b7dec02241dd9e4288b00af3a76a
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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