Sodium Hydroxide → 1-[(4-Methoxyphenyl)methyl]-3-methylidenepiperidin-2-one

HRID 65861노트

반응식

HRID 65861 반응식
Cl.[CH3:2][O:3][C:4]1[CH:20]=[CH:19][C:7]([CH2:8][N:9]2[CH2:18][CH2:17][CH2:16][CH:11]([C:12](OC)=O)[CH2:10]2)=[CH:6][CH:5]=1.[OH-:21].[Na+]>CO.O>[CH3:2][O:3][C:4]1[CH:20]=[CH:19][C:7]([CH2:8][N:9]2[CH2:18][CH2:17][CH2:16][C:11](=[CH2:12])[C:10]2=[O:21])=[CH:6][CH:5]=1

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 14181476methyl N-(p-methoxybenzyl)nipecotate hydrochloride

생성물 1

HCID 127744231-[(4-Methoxyphenyl)methyl]-3-methylidenepiperidin-2-one수율 71.4%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

A solution of methyl N-(p-methoxybenzyl)nipecotate hydrochloride (30.7 g) and 8.4 g of sodium hydroxide in 900 ml of methanol and 45 ml of water is stirred at room temperature for 17 hours. The solution is evaporated to dryness in vacuo, the residue diluted with toluene, and this again evaporated to dryness in vacuo. To the residue is added 1 liter of acetic anhydride and 140 ml of triethylamine, and the resulting mixture is heated under reflux for 4 hours. The reaction mixture is evaporated to dryness in vacuo, the residue taken up in chloroform, washed with water, dried, and concentrated in vacuo. The residual oil is chromatographed on silica gel using 1:1 hexane-ethyl acetate as the eluant, and yields 16.9 g of 1-(p-methoxybenzyl)-3-methylene-2-piperidone as a chromatographically pure yellow oil. Alternatively, the oil can be distilled to give analytically pure 1-(p-methoxybenzyl)-3-methylene-2-piperidone, b.p. 145°-155°/0.05 mm.

후처리

  1. customThe solution is evaporated to dryness in vacuo
  2. additionthe residue diluted with toluene
  3. customthis again evaporated to dryness in vacuo
  4. additionTo the residue is added 1 liter of acetic anhydride and 140 ml of triethylamine
  5. temperaturethe resulting mixture is heated
  6. temperatureunder reflux for 4 hours
  7. customThe reaction mixture is evaporated to dryness in vacuo
  8. washwashed with water
  9. customdried
  10. concentrationconcentrated in vacuo
  11. customThe residual oil is chromatographed on silica gel using 1:1 hexane-ethyl acetate as the eluant

출처 및 근거

ORD 기록
ord-d834cf21eb414ecf92e9448bc5ae5c4e
출처 데이터셋
uspto-grants-1978_12
특허 번호
US04129571

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