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

HRID 866058ノート

反応式

HRID 866058 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9392da3f598a4280866734ccf0ec5d14
出典データセット
uspto-grants-1996_10
特許番号
US05569664

反応ノート

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