Imidazole → 1-Adamantyl 1-imidazolylmethyl ketone

HRID 259307

Reaction equation

HRID 259307 reaction equation
Br[CH2:2][C:3]([C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]3)[CH2:6]1)[CH2:12]2)=[O:4].CN(C)C=O.[NH:20]1[CH:24]=[CH:23][N:22]=[CH:21]1>O>[NH:20]1[CH:24]=[CH:23][N:22]=[C:21]1[CH2:2][C:3]([C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]3)[CH2:6]1)[CH2:12]2)=[O:4]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 6228Dimethylformamide2×HCID 197820Bromomethyl tricyclo[3.3.1.13,7]dec-1-yl ketone

Product 1

HCID 433411781-Adamantyl 1-imidazolylmethyl ketone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5 g. of 1-adamantyl bromomethyl ketone in 10 ml. of dimethylformamide is added dropwise with stirring and ice-cooling to 7 g. imidazole in 10 ml. dimethylformamide. The resulting solution is stirred overnight at room temperature and then poured into 250 ml. water. The precipitate which forms is filtered off, washed with water and air dried. Thereafter the resulting residue is chromatographed on silica gel to effect purification. Elution with 10% acetone in dichloromethane yields 1-adamantyl 1-imidazolylmethyl ketone, M.P. 128.5°-129.5° C.

Workup

  1. temperatureice-cooling to 7 g
  2. stirringThe resulting solution is stirred overnight at room temperature
  3. additionpoured into 250 ml
  4. filtrationThe precipitate which forms is filtered off
  5. washwashed with water and air
  6. customdried
  7. customThereafter the resulting residue is chromatographed on silica gel
  8. custompurification
  9. washElution with 10% acetone in dichloromethane

Sources & evidence

ORD record
ord-b47529ff2e8c445b9a39986abbb92714
Source dataset
uspto-grants-1977_07
Patent number
US04036975

Linked notes

Loading…