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

HRID 1059540Notes

Reaction equation

HRID 1059540 reaction equation
[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]

Participants

3

Reactant 2

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

Product 1

HCID 54264041N-(3-cyanophenyl)-N'-(piperidin-3-yl)cycloheptylureaYield 104.8%

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d4b544dbb7844821b69f5cef194fb561
Source dataset
uspto-grants-2003_02
Patent number
US06521614B1

Reaction notes

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