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

HRID 1387142Notes

Reaction equation

HRID 1387142 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-3ad0fce7c8c64d889c793e43c286d8e7
Source dataset
uspto-grants-2001_07
Patent number
USRE037303E1

Reaction notes

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