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

HRID 1612841노트

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HRID 1612841 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
120 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5c072b6699774af5b33fab6be2d33b39
출처 데이터셋
uspto-grants-1993_03
특허 번호
US05190959

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