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Diisopropylethylamine → 1-[3-(4-Cyanobenzyl)-3H-imidazol-4-ylmethyl]-4-(3-methylbenzyl)piperidine-4-carbonitrile

HRID 443277
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 443277
Cl.[CH3:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[CH2:6][C:7]1([C:13]#[N:14])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.Cl.[C:19]([C:21]1[CH:34]=[CH:33][C:24]([CH2:25][N:26]2[C:30]([CH2:31]Cl)=[CH:29][N:28]=[CH:27]2)=[CH:23][CH:22]=1)#[N:20].C(N(C(C)C)CC)(C)C>C(#N)C>[C:19]([C:21]1[CH:22]=[CH:23][C:24]([CH2:25][N:26]2[C:30]([CH2:31][N:10]3[CH2:11][CH2:12][C:7]([CH2:6][C:5]4[CH:15]=[CH:16][CH:17]=[C:3]([CH3:2])[CH:4]=4)([C:13]#[N:14])[CH2:8][CH2:9]3)=[CH:29][N:28]=[CH:27]2)=[CH:33][CH:34]=1)#[N:20]
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Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 97953574-((5-(Chloromethyl)-1H-imidazol-1-yl)methyl)benzonitrile hydrochlorideHCID 211932254-(3-Methylbenzyl)piperidine-4-carbonitrile hydrochloride

Produkt 1

HCID 211932131-[3-(4-Cyanobenzyl)-3H-imidazol-4-ylmethyl]-4-(3-methylbenzyl)piperidine-4-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Versuchsvorschrift

A solution of 4-(3-methylbenzyl)piperidine-4-carbonitrile hydrochloride salt (129 mg, 0.51 mmol), 1-(4-cyanobenzyl)-5-chloromethylimidazole hydrochloride salt (135 mg, 0.51 mmol; Example 52, Step D), and diisopropylethylamine (440 mL, 2.5 mmol) in anhydrous acetonitrile (5 mL) was heated under reflux overnight. The resultant mixture was concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with a 85:15 v/v mixture of chloroform saturated with ammonia gas and hexhne. After collection and concentration of appropriate fractions, the residue was triturated with a mixture of ethyl acetate and diethyl ether. The white solid precipitated was filtered to provide the title compound.

Aufarbeitung

  1. temperatureunder reflux overnight
  2. concentrationThe resultant mixture was concentrated under vacuum
  3. additionThe residue was subjected to column chromatography on silica gel eluting with a 85:15 v/v mixture of chloroform saturated with ammonia gas and hexhne
  4. customAfter collection and concentration of appropriate fractions
  5. customthe residue was triturated with a mixture of ethyl acetate and diethyl ether
  6. customThe white solid precipitated
  7. filtrationwas filtered

Quellen und Nachweise

ORD-Eintrag
ord-4b026e306d304e1381e02a63c0bab792
Quelldatensatz
uspto-grants-1999_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05891889

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