N,N'-Dicyclohexylurea → Tyramine

HRID 609528Notes

Reaction equation

HRID 609528 reaction equation
ON1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=O.[CH:9]1([N:15]=C=NC2CCCCC2)CCCC[CH2:10]1.N=C=N.C(NC1CCCCC1)(N[CH:30]1CCCC[CH2:31]1)=O>>[NH2:15][CH2:9][CH2:10][C:3]1[CH:4]=[CH:5][C:6]([OH:7])=[CH:31][CH:30]=1

Participants

5

Reactant 4

HCID 4277N,N'-DicyclohexylureaHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 160435Carbodiimide

Product 1

HCID 5610Tyramine

Conditions

Temperature
70 °C

Procedure

Formation of the tyramide of compound 111, is as follows. N-hydroxysuccinimide (33 mg) is dissolved in the reaction mixture prepared above by heating to 70° C., then dicyclohexylcarbodiimide (61 mg) is added. This is reacted at 70° C. for 90 minutes, an additional amount (6 mg) of the carbodiimide is added and the reaction is continued for another 30 minutes. The mixture is cooled to 0° C. and the precipitated dicyclohexylurea is settled by centrifugation. The supernatant, containing 6-(-4'-N-hydroxysuccinimidyl carboxy phenyl)-3,8-bis bromoacetamidyl-5 -methylphenanthridinium chloride (IV) is recovered. A solution of tyramine [4-(2'-amino)ethylphenol] (1.0 g) in water (5 ml) is formed by bringing it to pH 7 by addition of concentrated HCl. This solution is added to the supernatant containing compound IV and reacted at room temperature for one hour. This mixture is then reduced to a red oil by evacuation at 60° C., and is then extracted with water to remove excess tyramine. Compound (VI) is then recrystalized from ethanol-acidified with HCl.

Workup

  1. customprepared above
  2. customThis is reacted at 70° C. for 90 minutes
  3. temperatureThe mixture is cooled to 0° C.
  4. customis recovered

Sources & evidence

ORD record
ord-0c4a6676a21a42ebb6bd30574e7f0d2b
Source dataset
uspto-grants-1999_12
Patent number
US05998135

Reaction notes

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