Dicyclohexylamine → HCID 7864499, compound

HRID 1902501Notes

Reaction equation

HRID 1902501 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-:3])=[O:2].C1(NC2CCCCC2)CCCCC1.Cl[CH2:27][N:28]1[C:32](=[O:33])[C:31]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]2[C:29]1=[O:38]>CN(C=O)C>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([O:8][CH2:27][N:28]1[C:29](=[O:38])[C:30]2=[CH:37][CH:36]=[CH:35][CH:34]=[C:31]2[C:32]1=[O:33])=[O:7])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7582DicyclohexylamineHCID 110872-Nitrobenzoic acidHCID 87154Chloromethylphthalimide

Product 1

HCID 7864499HCID 7864499, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

o-Nitrobenzoic acid (10.0 g) and dicyclohexylamine (11.0 g) were added in sequence to 100 ml DMF, more solvent being necessary to dissolve the resulting salt. N-(Chloromethyl)phthalimide was added and the mixture stirred for 24 hours. The product was precipitated out with water. Recrystallization from ethyl acetate/cyclohexane yielded 15.3 g (83%) of the ester, m.p. 159°-160° C.

Workup

  1. dissolutionto dissolve the resulting salt
  2. customThe product was precipitated out with water
  3. customRecrystallization from ethyl acetate/cyclohexane

Sources & evidence

ORD record
ord-81752663ad2146608199782dfaba1162
Source dataset
uspto-grants-1982_12
Patent number
US04363865

Reaction notes

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