Water → 1-(3,4-Dimethoxy-phenyl)-piperidine-4-one

HRID 2245344노트

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HRID 2245344 반응식
[I-].C([N+]1(C)[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]1)C1C=CC=CC=1.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][C:25]=1[O:26][CH3:27])[NH2:22].C(=O)([O-])[O-].[K+].[K+].O>C(O)C.C(=O)([O-])[O-].[K+].[K+]>[CH3:17][O:18][C:19]1[CH:20]=[C:21]([N:22]2[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]2)[CH:23]=[CH:24][C:25]=1[O:26][CH3:27]

참가 물질

7

반응물 4

HCID 962Water2회HCID 11430Potassium CarbonateHCID 227703,4-DimethoxyanilineHCID 110780641-Benzyl-1-methyl-4-oxopiperidinium iodide

생성물 1

HCID 220002541-(3,4-Dimethoxy-phenyl)-piperidine-4-one수율 61.8%

시약·촉매·용매 2

HCID 11430Potassium Carbonate촉매HCID 702Ethanol용매

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온도
100 °C

실험 절차

A slurry of 1-benzyl-1-methyl-4-oxo-piperidinium iodide (9270 mg), 3,4-dimethoxy aniline (3900 mg) and anhydrous potassium carbonate (437 mg) in ethanol (90 ml)/water (45 ml) were heated to reflux for 6 hours. Additional potassium carbonate (200 mg) was added and the reaction was heated to 100° C. over night. Water (50 ml) was added to the reaction mixture, which was extracted three times with DCM. The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered and the solvent was evaporated in vacuo to leave the crude product as a dark oil. The residue was purified by column chromatography (ethyl acetate/hexanes=1:1) to yield the product as a yellow solid (3700 mg). MS (ESI): 236.1 (MH+).

후처리

  1. temperatureto reflux for 6 hours
  2. extractionwas extracted three times with DCM
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated in vacuo
  7. customto leave the crude product as a dark oil
  8. customThe residue was purified by column chromatography (ethyl acetate/hexanes=1:1)

출처 및 근거

ORD 기록
ord-d742b2973ace485ca544ba4a79fd708c
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07683079B2

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