Cyclohexylamine → HCID 14990702, compound

HRID 2166053Notes

Reaction equation

HRID 2166053 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[CH:10]2)=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].[CH:17]1([NH2:23])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>>[CH:17]1([NH:23][C:2]2[CH:7]=[CH:6][C:5]([CH2:8][N:9]3[CH:13]=[CH:12][N:11]=[CH:10]3)=[CH:4][C:3]=2[N+:14]([O-:16])=[O:15])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

3

Reactant 2

HCID 7965CyclohexylamineHCID 14990689HCID 14990689, compound

Product 1

HCID 14990702HCID 14990702, compoundYield 93.8%

Procedure

A mixture of 8 parts of 1-[(4-chloro-3-nitrophenyl)methyl]-1H-imidazole and 42 parts of cyclohexanamine was stirred for 2 hours at reflux temperature. The mixture was evaporated and the residue was stirred in 2,2'-oxybispropane. The precipitated product was filtered off, washed with water and 2,2'-oxybispropane and purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was stirred in a mixture of 2,2'-oxybispropane and ethyl acetate. The product was filtered off, washed with ethyl acetate and 2,2'-oxybispropane and dried in vacuo at 60° C., yielding 9.5 parts (93.8%) of N-cyclohexyl-4-(1H-imidazol-1-yl-methyl)-2-nitrobenzenamine; mp. 121.1° C. (int. 146).

Workup

  1. temperatureat reflux temperature
  2. customThe mixture was evaporated
  3. stirringthe residue was stirred in 2,2'-oxybispropane
  4. filtrationThe precipitated product was filtered off
  5. washwashed with water and 2,2'-oxybispropane
  6. custompurified by column chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated
  10. stirringThe residue was stirred in a mixture of 2,2'-oxybispropane and ethyl acetate
  11. filtrationThe product was filtered off
  12. washwashed with ethyl acetate and 2,2'-oxybispropane
  13. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-ec7efef1d726465680dcf8efd088443c
Source dataset
uspto-grants-1990_07
Patent number
US04943574

Reaction notes

Loading…