Cyclopentylamine → HCID 9841980, compound

HRID 1857463Notes

Reaction equation

HRID 1857463 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:4]=[C:5]([NH:13][C:14](=[N:22][C:23]#[N:24])OC2C=CC=CC=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(#N)C.[CH:30]1([NH2:35])[CH2:34][CH2:33][CH2:32][CH2:31]1>>[C:23]([NH:22][C:14]([NH:13][C:5]1[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=[C:3]([C:2]([F:1])([F:25])[F:26])[CH:4]=1)=[N:35][CH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1)#[N:24]

Participants

4

Reactant 3

HCID 2906CyclopentylamineHCID 6342AcetonitrileHCID 178512266HCID 178512266, compound

Product 1

HCID 9841980HCID 9841980, compoundYield 82%

Conditions

Temperature
85 °C

Procedure

To a suspension of N-(3,5-bis(trifluoromethyl)phenyl)-N'-cyano-O-phenylisourea (0.400 g, 1.1 mmol) in dry acetonitrile (2.5 ml) triethylamine (0.164 ml, 1.2 mmol) and cyclopentylamine (0.116 ml, 1.2 mmol) was added. The homogenous solution was stirred at 85° C. under N2 for 3.5 h. The solvent was evaporated, and the residue was dissolved in ethyl acetate and washed with water twice. The organic layer was dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography using ethyl acetate/heptane 1:2 to give the title compound. Yield 82% (0.320 g). mp 156-159° C.

Workup

  1. additionwas added
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with water twice
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-cbd2b2c12d38440eb3b1030934e91455
Source dataset
uspto-grants-2000_11
Patent number
US06147098

Reaction notes

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