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

HRID 2273081ノート

反応式

HRID 2273081 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.[OH:13][CH:14]1[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]1>C1COCC1>[CH3:20][N:17]1[CH2:18][CH2:19][CH:14]([O:13][C:4]2[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][N:5]=2)[CH2:15][CH2:16]1

参加物

5

反応物 3

HCID 24758Sodium hydride2 回HCID 660484-Piperidinol, 1-methyl-HCID 783082-Chloro-5-nitropyridine

生成物 1

HCID 529048992-[(1-Methyl-4-piperidinyl)oxy]-5-nitropyridine収率 49.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

557 mg of NaH (14 mmol) suspended in 10 ml of THF are placed under nitrogen. The mixture is cooled to 0° C. and a solution of 1.5 g (9.3 mmol) of 2-chloro-5-nitropyridine and 1.28 g (11.1 mmol) of 4-hydroxy-1-methylpiperidine in 15 ml of THF is added dropwise. The reaction mixture is refluxed for 4 hours. After hydrolysing the excess NaH, the solvent is evaporated off under reduced pressure. The residue is taken up in ethyl acetate and washed with water and then with saturated NaCl solution. It is then dried over Na2SO4 and filtered, and the filtrate is evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with a DCM/MeOH mixture from (100/0 v/v) up to 100/4 v/v) to give 1.1 g of 2-(1-methylpiperidin-4-yloxy)-5-nitropyridine.

後処理

  1. temperatureThe reaction mixture is refluxed for 4 hours
  2. customthe solvent is evaporated off under reduced pressure
  3. washwashed with water
  4. dry with materialIt is then dried over Na2SO4
  5. filtrationfiltered
  6. customthe filtrate is evaporated under reduced pressure
  7. customThe residue is chromatographed on silica gel
  8. washeluting with a DCM/MeOH mixture from (100/0 v/v) up to 100/4 v/v)

出典と根拠

ORDレコード
ord-4d9e1ae15a884949b0e7493e37eef7ff
出典データセット
uspto-grants-2015_09
特許番号
US09120812B2

反応ノート

読み込み中…