1-Methyl-2-[2-(2-nitrophenyl)ethenyl]pyridin-1-ium iodide → 2-(2-Aminophenethyl)-1-methylpiperidine

HRID 1579333ノート

反応式

HRID 1579333 の反応式
[I-].[N+:2]([C:5]1[CH:19]=[CH:18][CH:17]=[CH:16][C:6]=1[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N+:10]=1[CH3:15])([O-])=O>[Pt]=O.C(O)C>[NH2:2][C:5]1[CH:19]=[CH:18][CH:17]=[CH:16][C:6]=1[CH2:7][CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]1[CH3:15]

参加物

4

反応物 1

HCID 667604421-Methyl-2-[2-(2-nitrophenyl)ethenyl]pyridin-1-ium iodide

生成物 1

HCID 110852822-(2-Aminophenethyl)-1-methylpiperidine収率 87%

試薬・触媒・溶媒 2

HCID 82844Platinum oxide (PtO)触媒HCID 702Ethanol溶媒

実験手順

A suspension of 2-(o-nitrostyryl)-1-methylpyridinium iodide (40.5 mg., 0.11 mole) prepared according to the method of L. Horwitz, J. Org. Chem., 21, 1039 (1956) in 200 ml. of ethanol is hydrogenated in a Parr hydrogenation apparatus employing 0.3 g. of platinum oxide catalyst while maintaining a reaction temperature of from about 50° to 75°C. When the hydrogen uptake ceases (about 3 hours), the reduction mixture is filtered, the filtrate evaporated and the resulting residue taken up in 500 ml. of water. The aqueous solution is basified with 40% sodium hydroxide and extracted with several 200 ml. portions of ether. Ethereal extracts are combined, washed with water, dried over magnesium sulfate, and the ether evaporated. Distillation of the residue thus obtained provides 20.8 g. (87% yield) of 2-(o-aminophenethyl)-1-methylpiperidine base having a boiling point of 121°-125°C. at 0.04 mm.

後処理

  1. customprepared
  2. filtrationWhen the hydrogen uptake ceases (about 3 hours), the reduction mixture is filtered
  3. customthe filtrate evaporated
  4. extractionextracted with several 200 ml
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. customthe ether evaporated
  8. distillationDistillation of the residue
  9. customthus obtained
  10. customprovides 20.8 g

出典と根拠

ORDレコード
ord-efad556d571d48d6abf4bb18223213b8
出典データセット
uspto-grants-1976_01
特許番号
US03931195

反応ノート

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