Sulfuric Acid → 4-(Phenyl-2-pyridylmethoxy)-1-[3-(2-nitrophenoxy)propyl]piperidine

HRID 1612841ノート

反応式

HRID 1612841 の反応式
[C:1]1([CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O[CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[N+:32]([O-:34])=[O:33])[CH2:18][CH2:17]1.S(=O)(=O)(O)O.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:1]1([CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[O:8][CH:16]2[CH2:17][CH2:18][N:19]([CH2:22][CH2:23][CH2:24][O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[N+:32]([O-:34])=[O:33])[CH2:20][CH2:21]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

6

反応物 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 315585Phenyl(pyridin-2-yl)methanolHCID 197767934-Hydroxy-1-[3-(2-nitrophenoxy)propyl]piperidine

生成物 1

HCID 197768194-(Phenyl-2-pyridylmethoxy)-1-[3-(2-nitrophenoxy)propyl]piperidine収率 29.3%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
120 °C

実験手順

There was stirred at 120° C. for 4 hours a mixture of 6.74 g of phenyl-2-pyridylmethanol, 7.85 g of 4-hydroxy-1-[3-(2-nitrophenoxy)propyl]piperidine, 11.0 g of concentrated sulfuric acid and 15 ml of toluene. After cooling, the reaction solution was poured into ice water, made alkaline with an aqueous sodium hydroxide, and extracted with toluene. The extract was washed with water, and toluene was removed under reduced pressure. The residue was eluted with ethyl acetate-ethanol-dichloromethane (1:1:1) by silica gel column chromatography to give 3.67 g of oily 4-(phenyl-2-pyridylmethoxy)-1-[3-(2-nitrophenoxy)propyl]piperidine.

後処理

  1. temperatureAfter cooling
  2. extractionextracted with toluene
  3. washThe extract was washed with water, and toluene
  4. customwas removed under reduced pressure
  5. washThe residue was eluted with ethyl acetate-ethanol-dichloromethane (1:1:1) by silica gel column chromatography

出典と根拠

ORDレコード
ord-5c072b6699774af5b33fab6be2d33b39
出典データセット
uspto-grants-1993_03
特許番号
US05190959

反応ノート

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