Piperidine → HCID 54536072, 화합물

HRID 978762노트

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HRID 978762 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 54536072HCID 54536072, 화합물수율 79.5%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b1eb4f32e768454896e65fcbc9301be0
출처 데이터셋
uspto-grants-1987_05
특허 번호
US04665188

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