Cyclopentylamine → HCID 86067038, compound

HRID 250725Notes

Reaction equation

HRID 250725 reaction equation
[CH3:1][N:2]([O:15][CH3:16])[C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6](F)[CH:5]=1.[CH:17]1([NH2:22])[CH2:21][CH2:20][CH2:19][CH2:18]1.C(#N)C>Cl>[CH3:16][O:15][N:2]([CH3:1])[C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6]([NH:22][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:5]=1

Participants

5

Reactant 3

HCID 2906CyclopentylamineHCID 6342AcetonitrileHCID 57758083HCID 57758083, compound

Product 1

HCID 86067038HCID 86067038, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Combine N-[methyl]N-[methoxy]3-fluoro-4-nitrobenzamide (2.3 g, 10 mmol), cyclopentylamine (12.3 mL, 100 mmol) and acetonitrile (50 mL) and stir at room temperature for 6 hours. Dilute with 1N HCl and extract with ethyl acetate. Wash the organic layer sequentially with water and saturated aqueous sodium chloride, then dry over magnesium sulfate. Concentrate under reduced pressure to provide the desired compound as an orange solid (2.7 g, 92%).

Workup

  1. extractionextract with ethyl acetate
  2. washWash the organic layer sequentially with water and saturated aqueous sodium chloride
  3. dry with materialdry over magnesium sulfate
  4. concentrationConcentrate under reduced pressure

Sources & evidence

ORD record
ord-47f792c7a0824ddcb95f086460f770ef
Source dataset
uspto-grants-2011_01
Patent number
US07863310B2

Reaction notes

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