Piperidine → HCID 54536072、化合物

HRID 978762ノート

反応式

HRID 978762 の反応式
[O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[CH:4][C:3]1=2.[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]=O)[CH:18]=1.N1CCCCC1>C(O)(=O)C>[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]=[C:11]2[CH2:10][CH2:9][C:8]3[CH:7]=[C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[CH:4][C:3]=3[C:2]2=[O:1])[CH:18]=1

参加物

5

反応物 3

HCID 8082PiperidineHCID 103713-PyridinecarboxaldehydeHCID 13607596Ethyl 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate

生成物 1

HCID 54536072HCID 54536072、化合物収率 79.5%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
100 °C

実験手順

5.0 g of ethyl 5-oxo-5,6,7,8-tetrahydro-2-naphthalenecarboxylate was mixed with 2.5 g of 3-pyridinealdehyde, 10 ml of acetic acid and 10 ml of piperidine and then the mixture was stirred at 100° C. for 4 hours. The reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate. 10% Hydrochloric acid was added to the solution. The aqueous layer was separated and neutralized by addition of sodium bicarbonate. The mixture was extracted with chloroform. The extract was washed with water, dried and then concentrated in vacuo. The residue was purified by silica gel column chromatography to give 5.6 g of ethyl 6-(3-pyridylmethylidene)-5-oxo-5,6,7,8-tetrahydro-2-naphthalenecarboxylate as pale yellow crystals with m.p. 112°-114° C.

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. addition10% Hydrochloric acid was added to the solution
  4. customThe aqueous layer was separated
  5. additionneutralized by addition of sodium bicarbonate
  6. extractionThe mixture was extracted with chloroform
  7. washThe extract was washed with water
  8. customdried
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-b1eb4f32e768454896e65fcbc9301be0
出典データセット
uspto-grants-1987_05
特許番号
US04665188

反応ノート

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