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

HRID 1651557

反応式

HRID 1651557 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4ab03042306345c98aef76116f372020
出典データセット
uspto-grants-1990_05
特許番号
US04929618

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