Cyclopentylamine → HCID 178512267, compound

HRID 1857476Notes

Reaction equation

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

Participants

Conditions

Temperature: 82 °C

Procedure

To a solution of N-(3,5-dichlorophenyl)-N'-cyano-O-phenylisourea (0.8 mmol, 250 mg) in dry acetonitrile (2 ml), cyclopentylamine (0.9 mmol, 0.089 ml) and triethylamine (0.125 ml) were added. The mixture was stirred for 21/2 h at 82° C. under nitrogen. After concentration the residue was purified by flash chromatography (ethyl acetate/heptane 1:2) to give the title compound (160 mg, 66%) as crystals. Mp 147.5-148.5° C.; 1H-NMR (CDCl3): δ 1.45 (m, 2H), 1.65 (m, 4H), 2.05 (m, 2H), 4.11 (sextet, 1H), 5.1 (br, 1H), 7.2 (m, 3H), 8.02 ppm (br, 1H); EI SP/MS: 296 (M+), 298 (M+2), 300 (M+4). MA calc for C13H14Cl2N4 : C, 52.54%; H, 4.75%; N, 18.85%. Found: C, 52.17%; H, 4.71%; N, 18.50%.

Workup

concentrationAfter concentration the residue
customwas purified by flash chromatography (ethyl acetate/heptane 1:2)

Sources & evidence

ORD record: ord-d9df1a4ea8b443ca82ef1f58f957c763
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06147098

Reaction notes

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