Potassium Carbonate → 5-Chloro-2-[2-[4-[(4-chlorophenyl)-2-pyridylmethoxy]-1-piperidyl]ethylthio]benzoxazole

HRID 1651549노트

반응식

HRID 1651549 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][S:25][C:26]1[O:27][C:28]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:29]=2[N:30]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[Cl:35][C:32]1[CH:33]=[CH:34][C:28]2[O:27][C:26]([S:25][CH2:24][CH2:23][N:13]3[CH2:12][CH2:11][CH:10]([O:9][CH:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=4)[C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=4)[CH2:15][CH2:14]3)=[N:30][C:29]=2[CH:31]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 111411972-((4-Chlorophenyl)(4-piperidinyloxy)methyl)pyridineHCID 146721322-(2-Bromoethylthio)-5-chlorobenzoxazole

생성물 1

HCID 150558525-Chloro-2-[2-[4-[(4-chlorophenyl)-2-pyridylmethoxy]-1-piperidyl]ethylthio]benzoxazole수율 54%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

After 2.00 g (6.60 mmol) of 4-[(4-chlorophenyl)-2-pyridylmethoxy]piperidine and 2.39 g (8.17 mmol) of 2-(2-bromoethylthio)-5-chlorobenzoxazole were dissolved in 10 ml of dioxane, 1.10 g (7.96 mmol) of potassium carbonate was added to the mixed solution, and the mixture was stirred at an oil bath temperature of 75° to 80° C. for 6 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 with a mixed solution of chloroform and methanol in the volume ratio 50:1 as an eluent. The desired fraction was concentrated to give 1.83 g (54%) of 5-chloro-2-[2-[4-[(4-chlorophenyl)-2-pyridylmethoxy]-1-piperidyl]ethylthio]benzoxazole as an oily product.

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 with a mixed solution of chloroform and methanol in the volume ratio 50:1 as an eluent
  5. concentrationThe desired fraction was concentrated

출처 및 근거

ORD 기록
ord-149cdd9d0efd45179a0acaac17bcaa07
출처 데이터셋
uspto-grants-1990_05
특허 번호
US04929618

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