Sodium hydride → 2-[(1-Methyl-4-piperidinyl)oxy]-5-nitropyridine

HRID 1512103ノート

反応式

HRID 1512103 の反応式
[H-].[Na+].Cl[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][N:5]=1.[CH3:13][N:14]1[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH2:15]1>O1CCCC1>[CH3:13][N:14]1[CH2:19][CH2:18][CH:17]([O:20][C:4]2[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][N:5]=2)[CH2:16][CH2:15]1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 660484-Piperidinol, 1-methyl-HCID 783082-Chloro-5-nitropyridine

生成物 1

HCID 529048992-[(1-Methyl-4-piperidinyl)oxy]-5-nitropyridine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a mixture of sodium hydride (189 mg, 4.73 mmol) in anhydrous tetrahydrofuran (2 mL) at 0° C., a solution of 2-chloro-5-nitropyridine (500 mg, 3.16 mmol) and 1-methylpiperidin-4-ol (455 mg, 3.96 mmol) in anhydrous tetrahydrofuran (4 mL) was added dropwise. The reaction was heated reflux for 16 h. The THF was evaporated and water (100 mL) and EtOAc (200 mL) were added. The aqueous layer was extracted with EtOAc (200 mL). The organic layers were combined, washed with brine, dried over sodium sulfate and concentrated to give a brown oil. Purification by silica gel column chromatography using 3% methanol/methylene chloride yielded 2-(1-methylpiperidin-4-yloxy)-5-nitropyridine as a yellow solid, (367 mg, 49%). LC/MS (m/z): 238.0 (MH+), Rt 1.59 minutes.

後処理

  1. temperatureThe reaction was heated
  2. temperaturereflux for 16 h
  3. customThe THF was evaporated
  4. additionwater (100 mL) and EtOAc (200 mL) were added
  5. extractionThe aqueous layer was extracted with EtOAc (200 mL)
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customto give a brown oil
  10. customPurification by silica gel column chromatography

出典と根拠

ORDレコード
ord-15026e6255c94293934e938eb4c34de9
出典データセット
uspto-grants-2012_07
特許番号
US08217035B2

反応ノート

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