Cyclopentylamine → N-Cyano-N'-(3-trifluoromethylphenyl)-N"-cyclopentylguanidine

HRID 1857472Notes

Reaction equation

HRID 1857472 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([NH:9][C:10](=[N:18][C:19]#[N:20])OC2C=CC=CC=2)[CH:6]=[CH:7][CH:8]=1.[CH:23]1([NH2:28])[CH2:27][CH2:26][CH2:25][CH2:24]1>ClCCl>[C:19]([NH:18][C:10]([NH:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:21])[F:22])[CH:4]=1)=[N:28][CH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1)#[N:20]

Participants

4

Reactant 2

HCID 2906CyclopentylamineHCID 178512251HCID 178512251, compound

Product 1

HCID 53903819N-Cyano-N'-(3-trifluoromethylphenyl)-N"-cyclopentylguanidineYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(3-Trifluoromethylphenyl)-N'-cyano-O-phenylisourea (1 mmol, 290 mg) was stirred for 19 h at 80° C. in cyclopentylamine (1 ml). After concentration of the cold reaction mixture, the residue was dissolved in dichloromethane, washed with 1 N aqueous HCl (2×), water, dried (Na2SO4) and concentrated. The residue was purified by column chromatography (heptane:ethyl acetate 3:1) to give the title compound (205 mg, 68%) as a syrup. Crystallisation from heptane:ethyl acetate 2:1 gave 147 mg (49%). Mp 111.5-113° C; 1H-NMR (CDCl3): δ 1.42 (m, 2H), 1.65 (m, 4H), 2.05 (m, 2H), 4.12 (sextet, 1H), 4.85 (br, 1H), 7.35 (br s,1H), 7.5 ppm (m, 4H); MA calc for C14H15F3N4 : C, 56.75%; H, 5.10%; N, 18.91%. Found: C, 56.48%; H, 5.08%; N, 18.65%.

Workup

  1. customAfter concentration of the cold reaction mixture
  2. washwashed with 1 N aqueous HCl (2×), water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (heptane:ethyl acetate 3:1)

Sources & evidence

ORD record
ord-384f6e00b4084381ba4804028cce0856
Source dataset
uspto-grants-2000_11
Patent number
US06147098

Reaction notes

Loading…