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Diisopropylethylamine → Methyl 1-[3-(4-cyanobenzyl)-3H-imidazol-4-ylmethyl]-4-(3-methylbenzyl)piperidine-4-carboxylate

HRID 443263
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HRID 443263 반응식
Cl.[CH3:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[CH2:6][C:7]1([C:13]([O:15][CH3:16])=[O:14])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.Cl.[C:21]([C:23]1[CH:36]=[CH:35][C:26]([CH2:27][N:28]2[C:32]([CH2:33]Cl)=[CH:31][N:30]=[CH:29]2)=[CH:25][CH:24]=1)#[N:22].C(N(C(C)C)CC)(C)C>C(#N)C>[C:21]([C:23]1[CH:24]=[CH:25][C:26]([CH2:27][N:28]2[C:32]([CH2:33][N:10]3[CH2:9][CH2:8][C:7]([CH2:6][C:5]4[CH:17]=[CH:18][CH:19]=[C:3]([CH3:2])[CH:4]=4)([C:13]([O:15][CH3:16])=[O:14])[CH2:12][CH2:11]3)=[CH:31][N:30]=[CH:29]2)=[CH:35][CH:36]=1)#[N:22]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 97953574-((5-(Chloromethyl)-1H-imidazol-1-yl)methyl)benzonitrile hydrochlorideHCID 21193291Methyl 4-(3-methylbenzyl)piperidine-4-carboxylate hydrochloride salt

생성물 1

HCID 15410567Methyl 1-[3-(4-cyanobenzyl)-3H-imidazol-4-ylmethyl]-4-(3-methylbenzyl)piperidine-4-carboxylate

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

실험 절차

A solution of methyl 4-(3-methylbenzyl)piperidine-4-carboxylate hydrochloride salt (142 mg, 0.5 mmol), 1-(4-cyanobenzyl)-5-chloromethylimidazole hydrochloride salt (135 mg, 0.5 mmol; Example 52, Step D), and diisopropylethylamine (0.26 mL, 1.5 mmol) in anhydrous acetonitrile (5 mL) was heated under reflux overnight. The resultant mixture was concentrated under vacuum, and the residue was partitioned between saturated aqueous sodium bicarbonate and ethyl acetate. The organic extract was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 5% methanol in chloroform. After collection and concentration of appropriate fractions, the residue was recrystallized from a mixture of ethyl acetate and hexane to provide the title compound as white solid.

후처리

  1. temperatureunder reflux overnight
  2. concentrationThe resultant mixture was concentrated under vacuum
  3. customthe residue was partitioned between saturated aqueous sodium bicarbonate and ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customAfter collection and concentration of appropriate fractions
  10. customthe residue was recrystallized from a mixture of ethyl acetate and hexane

출처 및 근거

ORD 기록
ord-077214a85e664cd18cc84147e6e4dd45
출처 데이터셋
uspto-grants-1999_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05891889

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