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

HRID 490186

반응식

HRID 490186 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.[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

참가 물질

6

반응물 4

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

생성물 1

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

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), 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)+.

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-7ff2b7dec02241dd9e4288b00af3a76a
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528134B2

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