Cyclohexanemethylamine → HCID 178512311, compound

HRID 744041Notes

Reaction equation

HRID 744041 reaction equation
C1C=CC(O[C:8](OC2C=CC=CC=2)=[N:9][C:10]#[N:11])=CC=1.[CH:19]1([CH2:25][NH2:26])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.[NH:27]1[CH:31]=[C:30]([CH2:32][CH2:33][CH2:34][NH2:35])[N:29]=[CH:28]1>C(#N)C>[C:10]([NH:9][C:8]([NH:35][CH2:34][CH2:33][CH2:32][C:30]1[N:29]=[CH:28][NH:27][CH:31]=1)=[N:26][CH2:25][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)#[N:11]

Participants

5

Reactant 3

HCID 76688CyclohexanemethylamineHCID 688090Diphenyl N-CyanocarbonimidateHCID 178510931HCID 178510931, compound

Product 1

HCID 178512311HCID 178512311, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5 mmol of diphenyl N-cyanocarbonimidate are stirred with 5 mmol of cyclohexylmethylamine in 20 ml of acetonitrile for 2 h at room temperature. 5 mmol of 3-(1H-imidazol-4-yl)propanamine are then added and the mixture is brought to reflux for 8 h. The solution is concentrated under vacuum until dryness and the residue taken up in 5% acetic acid and washed with diethyl ether. After having been basified, the solution is extracted several times with dichloromethane. The combined and concentrated organic phases are purified by chromatography. The title compound is obtained, after concentration, in the form of a dry foam from diethyl ether.

Workup

  1. temperatureto reflux for 8 h
  2. concentrationThe solution is concentrated under vacuum until dryness
  3. washwashed with diethyl ether
  4. extractionthe solution is extracted several times with dichloromethane
  5. customconcentrated organic phases are purified by chromatography

Sources & evidence

ORD record
ord-3f81d2206acb4adea3ef4638d98ab7c0
Source dataset
uspto-grants-1996_09
Patent number
US05559113

Reaction notes

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