Hydrochloric Acid → GT-2227

HRID 1276467Notes

Reaction equation

HRID 1276467 reaction equation
C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:8]2[CH:12]=[C:11]([CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[N:10]=[CH:9]2)C=CC=CC=1.Cl>C(O)C>[NH:8]1[CH:12]=[C:11]([CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[N:10]=[CH:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 70148757HCID 70148757, compound

Product 1

HCID 178440800GT-2227Yield 96.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

1-[1-Triphenylmethyl-1H-imidazol-4-yl]-6-cyclohexyl-cis-3-hexene (1 gram, 2.12 mmol) was dissolved in ethanol (20 ml). 2N HCl (60 ml) was added and the mixture heated at 90° C. for 1 hour. The reaction mixture was cooled, filtered and the filtrate neutralized with 10% NaOH solution and then partitioned between CHCl3 and water. The chloroform layer was separated, dried over Na2SO4, filtered and evaporated in vacuo to obtain the crude oil. The crude product was purified by silica gel column chromatography using MeOH/CHCl3, (10:90) to afford 475 mgs of 1-[1H-imidazol-4-yl]-6-cyclohexyl-cis-3-hexene (24). ##STR55## 4-(6-Cyclohexyl-cis-3-enyl)imidazole (24) 1H-NMR (300 MHz, CDCl3): δ7.52 (s, 1H), 6.76 (s, 1H), 5.38 (m, 2H), 2.65 (m, 2H), 2.36 (m, 2H), 1.98 (m, 2H), 1.64 (m, 5H), 1.22 -1.08 (m, 6H), 0.84 (m, 2H); Mass Spectrum (DCl/NH3): 233 (M+1)+, MW=232.3704, C15H24N2 ; CNH Analysis: Calc.: C: 77.58, H: 10.34, N: 12.06; Found: C: 76.14, H: 10.04, N: 11.95.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. custompartitioned between CHCl3 and water
  4. customThe chloroform layer was separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto obtain the crude oil
  9. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8c415eb842f342f5a70dac57a1154ac2
Source dataset
uspto-grants-2000_12
Patent number
US06166060

Reaction notes

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