1-Chloroethyl chloroformate → N-(3-cyanophenyl)-N'-(piperidin-3-yl)cycloheptylurea

HRID 1059540Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1059540
[C:1]([C:3]1[CH:4]=[C:5]([N:9]([CH:26]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[C:10]([NH:12][CH:13]2[CH2:18][CH2:17][CH2:16][N:15](CC3C=CC=CC=3)[CH2:14]2)=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2].ClC(OC(Cl)C)=O>>[C:1]([C:3]1[CH:4]=[C:5]([N:9]([CH:26]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[C:10]([NH:12][CH:13]2[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]2)=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Komponenten

3

Edukt 2

HCID 5213051-Chloroethyl chloroformateHCID 18630688n-(3-Cyanophenyl)-n'-((n-benzyl)piperidin-3-yl)cycloheptylurea

Produkt 1

HCID 54264041N-(3-cyanophenyl)-N'-(piperidin-3-yl)cycloheptylureaAusbeute 104,8 %

Versuchsvorschrift

A mixture of N-(3-cyanophenyl)-N′-((N-benzyl)piperidin-3-yl)cycloheptyl-urea (prepared in Example 60, 2.7 g, 6.98 mmol) and α-chloroethyl chloroformate (1.09 g, 7.65 mmol) was stirred at ambient temperature for 2.5 h, whereupon the reaction was complete as judged by TLC. The solvent was removed by evaporation in vaccuo and was replaced with methanol (40 mL). The reaction was heated at reflux until all of the newly formed intermediate was consumed as indicated by TLC. Evaporation of the solvent gave 2.49 g of N-(3-cyanophenyl)-N′-(piperidin-3-yl)cycloheptylurea; LRMS (M+H)+ m/z 299.

Aufarbeitung

  1. customThe solvent was removed by evaporation in vaccuo
  2. temperatureThe reaction was heated
  3. temperatureat reflux until all of the newly formed intermediate
  4. customwas consumed
  5. customEvaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-d4b544dbb7844821b69f5cef194fb561
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06521614B1

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