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Allyl bromide → HCID 23300004, 화합물

HRID 1952754
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인쇄 미리보기

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HRID 1952754 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2([CH3:28])[C:20](=[O:21])[NH:19][C:18]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)=[N:17]2)[CH2:11][CH2:10]1.[CH2:29](Br)[CH:30]=[CH2:31].[OH-].[K+].C1OCCOCCOCCOCCOCCOC1>O1CCCC1>[CH2:31]([N:19]1[C:20](=[O:21])[C:16]([CH2:15][N:12]2[CH2:13][CH2:14][N:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[CH2:10][CH2:11]2)([CH3:28])[N:17]=[C:18]1[C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)[CH:30]=[CH2:29]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 7841Allyl bromideHCID 14797Potassium HydroxideHCID 2855718-Crown-6HCID 23300006HCID 23300006, 화합물

생성물 1

HCID 23300004HCID 23300004, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 4-[4-(2-methoxyphenyl)piperazin-1-ylmethyl]-4-methyl-2-(3-pyridyl)-2-imidazolin-5-one (3.7 g; prepared in a similar manner to that described in Example 36), allyl bromide (1.05 ml), finely-powdered potassium hydroxide (0.79 g), 18-Crown-6 (0.26 g) and tetrahydrofuran (50 ml) was stirred at ambient temperature under nitrogen for 120 hours, then poured onto ice-water (30 ml). The product was extracted into ethyl acetate, the extracts were dried (MgSO4), and the solvent was removed in vacuo. The residue was purified by flash chromatography over silica using a 9:1 mixture of ethyl acetate and ethanol as eluant. Appropriate fractions were combined, and the solvents removed in vacuo to leave 1-allyl-4-[4-(2-methoxyphenyl)piperazin-1-ylmethyl]-4-methyl-2-(3-pyridyl)-2-imidazolin-5-one as an off-white solid (0.25 g), m.p. 66-69° C.

후처리

  1. customprepared in a similar manner to that
  2. additionpoured onto ice-water (30 ml)
  3. extractionThe product was extracted into ethyl acetate
  4. dry with materialthe extracts were dried (MgSO4)
  5. customthe solvent was removed in vacuo
  6. customThe residue was purified by flash chromatography over silica using
  7. additiona 9:1 mixture of ethyl acetate and ethanol as eluant
  8. customthe solvents removed in vacuo

출처 및 근거

ORD 기록
ord-c43a877ab27c4bcab88778da9c1b5f9f
출처 데이터셋
uspto-grants-2000_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06114334

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