Ethyl 4-piperidinecarboxylate → ethyl N-(2,6-dimethoxyphenylmethyl)piperidin-4-ylcarboxylate

HRID 1683837노트

반응식

HRID 1683837 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH2:11]Br.[NH:13]1[CH2:18][CH2:17][CH:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15][CH2:14]1.[F-].[K+]>C(#N)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH2:11][N:13]1[CH2:18][CH2:17][CH:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15][CH2:14]1

참가 물질

5

반응물 3

HCID 70770Ethyl 4-piperidinecarboxylateHCID 522689Potassium FluorideHCID 155569582-(Bromomethyl)-1,3-dimethoxybenzene

생성물 1

HCID 19040928ethyl N-(2,6-dimethoxyphenylmethyl)piperidin-4-ylcarboxylate수율 16.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A stirred solution of 4.7 grams (0.020 mole) of 2,6-dimethoxyphenylmethyl bromide, 3.2 grams (0.020 mole) of ethyl piperidin-4-ylcarboxylate, and 23.5 grams (0.200 mole) of 50% potassium fluoride on Celite® filter aid in 100 mL of acetonitrile was heated at reflux for about 18 hours, after which the reaction mixture was cooled and filtered. The filtrate was concentrated under reduced pressure to a residue, which was subjected to column chromatography on silica gel, with mixtures of ethyl acetate in hexane as eluants. The product-containing fractions were combined and concentrated under reduced pressure to a residue. The residue was analyzed using thin layer chromatography, which indicated that the residue was impure. The residue was again subjected to column chromatography on silica gel, with mixtures of ethyl acetate in hexane and methanol in ethyl acetate as eluants. The product-containing fractions were combined and concentrated under reduced pressure, yielding about one gram of ethyl N-(2,6-dimethoxyphenylmethyl)piperidin-4-ylcarboxylate. The NMR spectrum was consistent with the proposed structure.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for about 18 hours
  3. temperatureafter which the reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure to a residue, which
  6. concentrationconcentrated under reduced pressure to a residue
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-a139f7783188480298cdfc3e564ac19e
출처 데이터셋
uspto-grants-1997_06
특허 번호
US05639763

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