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

HRID 443263
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 443263
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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-077214a85e664cd18cc84147e6e4dd45
Quelldatensatz
uspto-grants-1999_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05891889

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