1,2-Diaminocyclohexane, cis- → HCID 90355899, compound

HRID 1470329Notes

Reaction equation

HRID 1470329 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C@@H:11]1([NH2:18])[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]1[NH2:17]>>[NH2:1][C:2]1[CH:9]=[C:8]([NH:17][C@@H:12]2[CH2:13][CH2:14][CH2:15][CH2:16][C@@H:11]2[NH2:18])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

3

Reactant 2

HCID 3429171,2-Diaminocyclohexane, cis-HCID 99421582-Amino-4-fluorobenzonitrile

Product 1

HCID 90355899HCID 90355899, compound

Conditions

Temperature
100 °C

Procedure

2-Amino-4-fluorobenzonitrile (200 mg, 1.47 mmol) and cis-cyclohexane-1,2-diamine (839 mg, 7.35 mmol) (Sigma-Aldrich; CAS: 1436-59-5) were added to a vial. The vial was then sealed and heated at 100° C. After 16 hours, the reaction mixture was cooled to room temperature and purified directly by silica gel chromatography (10-100% (10% methanol in DCM)/hexanes, linear gradient) to afford rel-2-amino-4-{[(1R,2S)-2-aminocyclohexyl]amino}benzonitrile. MS ESI calc'd. for C13H19N4 [M+H]+ 231. Found 231. 1H NMR (500 MHz, DMSO-d6) δ 6.97 (d, J=8.6 Hz, 1H), 5.97 (d, J=8.6 Hz, 1H), 5.89 (d, J=1.8 Hz, 1H), 5.85 (d, J=7.7 Hz, 1H), 5.48 (s, 2H), 3.32-3.19 (m, 1H), 3.15 (s, 2H), 3.03-2.90 (m, 1H), 1.64-1.33 (m, 6H), 1.33-1.14 (m, 2H).

Workup

  1. customThe vial was then sealed
  2. temperaturethe reaction mixture was cooled to room temperature
  3. custompurified directly by silica gel chromatography (10-100% (10% methanol in DCM)/hexanes, linear gradient)

Sources & evidence

ORD record
ord-3d76b25500d14fef85ea377b292388ff
Source dataset
uspto-grants-2015_04
Patent number
US09006444B2

Reaction notes

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