Formaldehyde → N-(3',6'-dihydro-2,4'-bipyridin-1'(2'H)-ylmethyl)-3-methoxybenzamide

HRID 490171

반응식

HRID 490171 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([NH2:8])=[O:7].C([O-])([O-])=O.[K+].[K+].[CH2:18]=O.Cl.[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]1[CH2:28][CH2:29][NH:30][CH2:31][CH:32]=1>C(O)C>[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]1[CH2:28][CH2:29][N:30]([CH2:18][NH:8][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:31][CH:32]=1

참가 물질

6

반응물 4

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 984873-MethoxybenzamideHCID 688728301',2',3',6'-Tetrahydro-2,4'-bipyridine hydrochloride

생성물 1

HCID 68874678N-(3',6'-dihydro-2,4'-bipyridin-1'(2'H)-ylmethyl)-3-methoxybenzamide수율 49%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

3-Methoxybenzamide (1.13 g, 7.5 mmol), K2CO3 (345 mg, 2.5 mmol), paraformaldehyde (0.5 g, 16 mmol), and 1′,2′,3′,6′-tetrahydro-2,4′-bipyridine hydrochloride (393 mg, 2 mmol) were combined in ethanol (25 ml) and refluxed for 18 hours. The reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure. The residue was partitioned between ethyl acetate (80 mL) and water (80 mL). The organic layer was washed with brine (2×50 mL), dried over MgSO4, filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (elution with ethyl acetate:ethanol, 9.0:1.0) to provide the title compound (180 mg, 49% yield). 1H NMR (300 MHz, DMSO-d6) δ 2.58 (m, 2H), 2.76 (t, 2H, J=6 Hz), 3.29 (m, 2H), 3.80 (s, 3H), 4.27 (d, 2H, J=6 Hz), 6.70 (m, 1H), 7.09 (m, 1H), 7.22 (m, 1H), 7.42 (m, 4H), 7.72 (m, 1H), 8.51 (m, 1H), 8.83 (t, 1H, J=6 Hz); MS (DCI/NH3) m/e 324 (M+H)+.

후처리

  1. temperaturerefluxed for 18 hours
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate (80 mL) and water (80 mL)
  4. washThe organic layer was washed with brine (2×50 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under reduced pressure
  8. customThe residue was purified by flash chromatography on silica gel (elution with ethyl acetate:ethanol, 9.0:1.0)

출처 및 근거

ORD 기록
ord-430c647e9998449c99bced5335b09bf6
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528134B2

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