Cyclopentylamine → N-(2-Chloro-4-pyridinyl)-N′-cyclopentylurea

HRID 619877Notes

Reaction equation

HRID 619877 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9](=[O:17])OC2C=CC=CC=2)[CH:5]=[CH:4][N:3]=1.[CH:18]1([NH2:23])[CH2:22][CH2:21][CH2:20][CH2:19]1>CC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([NH:23][CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:17])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 2906CyclopentylamineHCID 21247422Phenyl (2-chloropyridin-4-yl)carbamate

Product 1

HCID 14625237N-(2-Chloro-4-pyridinyl)-N′-cyclopentylureaYield 85.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred solution of 3.5 grams (0.0141 mole) of phenyl N-(2-chloro-4-pyridinyl)carbamate and 1.7 ml (0.0172 mole) of cyclopentylamine in 60 ml of acetone was heated under reflux for three hours. The reaction mixture was cooled and concentrated under reduced pressure to a residual oil. The oil was dissolved in 20 ml of methylene chloride and passed through a column of silica gel. Elution was accomplished with 5% and 10% acetone-methylene chloride. The appropriate fractions were combined and concentrated under reduced pressure to yield 2.9 grams of N-(2-chloro-4-pyridinyl)-N'-cyclopentylurea; m.p. 119°-121° C. The nmr spectrum was consistent with the proposed structure.

Workup

  1. temperatureunder reflux for three hours
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated under reduced pressure to a residual oil
  4. dissolutionThe oil was dissolved in 20 ml of methylene chloride
  5. washElution
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3dad35d76aeb4b838342935cc8eec840
Source dataset
uspto-grants-1989_04
Patent number
US04818271

Reaction notes

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