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

HRID 490171

反応式

HRID 490171 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-430c647e9998449c99bced5335b09bf6
出典データセット
uspto-grants-2009_05
特許番号
US07528134B2

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