Potassium Carbonate → Ethyl 3-[4-[(4-chlorophenyl)-2-pyridylmethoxy]-1-piperidyl]-propionate

HRID 1651557

반응식

HRID 1651557 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[O:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1.Br[CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[O:9][CH:10]2[CH2:11][CH2:12][N:13]([CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:14][CH2:15]2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 68320Ethyl 3-bromopropionateHCID 111411972-((4-Chlorophenyl)(4-piperidinyloxy)methyl)pyridine

생성물 1

HCID 15055865Ethyl 3-[4-[(4-chlorophenyl)-2-pyridylmethoxy]-1-piperidyl]-propionate수율 67%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
80 °C

실험 절차

2.00 g (6.61 mmol) of 4-[(4-chlorophenyl)-2-pyridylmethoxy]piperidine and 1.43 g (7.90 mmol) of ethyl 3-bromopropionate were dissolved in 10 ml of dioxane, and 1.09 g (7.89 mmol) of potassium carbonate was added to the mixed solution, and then the mixture was stirred under heating at an oil bath temperature of around 80° C. for 8 hours. After the reaction, the insolubles were filtered off, and the filtrate was concentrated under reduced pressure. The residue was separated by silica gel column chromatography using a solvent mixture of chloroform and methanol in the volume ratio 19:1 as are eluent. The desired fraction was concentrated under reduced pressure to give 1.78 g (67%) of ethyl 3-[4-[(4-chlorophenyl)-2-pyridylmethoxy]-1-piperidyl]-propionate.

후처리

  1. customAfter the reaction
  2. filtrationthe insolubles were filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was separated by silica gel column chromatography
  5. additiona solvent mixture of chloroform and methanol in the volume ratio 19:1
  6. concentrationThe desired fraction was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-4ab03042306345c98aef76116f372020
출처 데이터셋
uspto-grants-1990_05
특허 번호
US04929618

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