Toluene → 3-Cyclohexylpropyl 3-(1H-imidazol-4-yl)propyl ether

HRID 726227

Reaction equation

HRID 726227 reaction equation
C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:8]2[CH:12]=[C:11]([CH2:13][CH2:14][CH2:15][O-:16])[N:10]=[CH:9]2)C=CC=CC=1.[Na+].C1(C)C=CC=CC=1.C1OCCOCCOCCOCCOC1.Cl[CH2:53][CH2:54][CH2:55][CH:56]1[CH2:61][CH2:60][CH2:59][CH2:58][CH2:57]1>C(OCC)C>[NH:8]1[CH:12]=[C:11]([CH2:13][CH2:14][CH2:15][O:16][CH2:53][CH2:54][CH2:55][CH:56]2[CH2:61][CH2:60][CH2:59][CH2:58][CH2:57]2)[N:10]=[CH:9]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 3633615-Crown-5HCID 70762(3-Chloropropyl)cyclohexaneHCID 23682245sodium 3-(1-triphenylmethyl-1H-imidazol-4-yl)propanolate

Product 1

HCID 1784208943-Cyclohexylpropyl 3-(1H-imidazol-4-yl)propyl ether

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
75 °C

Procedure

5 mmol of sodium 3-[1-(triphenylmethyl)imidazol-4-yl]propoxide in 10 ml of toluene containing 0.5 mmol of 15-Crown-5 and 5 mmol of (3-chloropropyl)cyclohexane are mixed and the mixture is stirred for 24 h at 75° C. The suspension is concentrated under vacuum, the product obtained is dissolved in diethyl ether, the solution is filtered and the residue washed with petroleum ether (40°-60° C.). The filtrate obtained is concentrated and maintained for 1 h at the boiling point in a 2N aqueous/alcohol (ethanol/water) hydrochloric acid solution. The ethanol is removed under a low vacuum and the precipitate is filtered under vacuum. The solution is basified, extracted with dichloromethane and the organic phase is concentrated. The title compound obtained is recrystallized in the hydrogenmaleate form from ethanol/ diethyl ether.

Workup

  1. concentrationThe suspension is concentrated under vacuum
  2. customthe product obtained
  3. filtrationthe solution is filtered
  4. washthe residue washed with petroleum ether (40°-60° C.)
  5. customThe filtrate obtained
  6. concentrationis concentrated
  7. temperaturemaintained for 1 h at the boiling point in a 2N aqueous/alcohol (ethanol/water) hydrochloric acid solution
  8. customThe ethanol is removed under a low vacuum
  9. filtrationthe precipitate is filtered under vacuum
  10. extractionextracted with dichloromethane
  11. concentrationthe organic phase is concentrated

Sources & evidence

ORD record
ord-f5a0acaa7b8148ff8e717fa1d8a06de0
Source dataset
uspto-grants-1998_01
Patent number
US05708171

Linked notes

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