Hydrochloric Acid → HCID 178420888, compound

HRID 1276468Notes

Reaction equation

HRID 1276468 reaction equation
C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:8]2[CH:12]=[C:11]([CH2:13][CH2:14][C:15]#[C: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>[CH:19]1([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:11]2[N:10]=[CH:9][NH:8][CH:12]=2)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 184283751-[1-triphenylmethyl-1H-imidazol-4-yl]-6-cyclohexyl-3-hexyne

Product 1

HCID 178420888HCID 178420888, compoundYield 34.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

1-[1-Triphenylmethyl-1H-imidazol-4-yl]-6-cyclohexyl-3-hexyne (0.629 g, 1.33 mmol) was suspended in ethyl alcohol (3 ml). 2N HCl (25 ml) was added and the reaction mixture heated at 90° C. for 1 hr. The reaction mixture was cooled, filtered through a pad of celite and the filtrate evaporated in vacuo. The residue was dissolved in methanol (20 ml). 10% Pd(C) (0.139 g) and ammonium formate (1.5 g) were added, and the reaction mixture heated at 65° C. under N2 for 6.5 hours. The reaction mixture was cooled, filtered through a pad of celite and the methanol filtrate concentrated. The residue was partitioned between CH2Cl2 and 10% NaOH solution (100 ml, 1:1). The CH2Cl2 layer was separated, washed with water (50 ml), dried over MgSO4, filtered and evaporated in vacuo. Purification by flash chromatography using ethyl acetate as eluent gave 108 mgs of final product. ##STR72## 4-(6-Cyclohexylhexyl)imidazole (41) 1H-NMR (300 MHz, CD3OD): δ7.53 (s, 1H), 6.73 (s, 1H), 2.56 (t, J=7.5 Hz, 2H), 1.65 (m, 7H), 1.40-1.10 (m, 12H), 0.89 (m, 2H); Mass Spectrum: (DCl/NH3): 235 (M+1)+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered through a pad of celite
  3. customthe filtrate evaporated in vacuo
  4. dissolutionThe residue was dissolved in methanol (20 ml)
  5. addition10% Pd(C) (0.139 g) and ammonium formate (1.5 g) were added
  6. temperaturethe reaction mixture heated at 65° C. under N2 for 6.5 hours
  7. temperatureThe reaction mixture was cooled
  8. filtrationfiltered through a pad of celite
  9. concentrationthe methanol filtrate concentrated
  10. customThe residue was partitioned between CH2Cl2 and 10% NaOH solution (100 ml, 1:1)
  11. customThe CH2Cl2 layer was separated
  12. washwashed with water (50 ml)
  13. dry with materialdried over MgSO4
  14. filtrationfiltered
  15. customevaporated in vacuo
  16. customPurification by flash chromatography

Sources & evidence

ORD record
ord-d46bfab3ef214732ab1672936008b59e
Source dataset
uspto-grants-2000_12
Patent number
US06166060

Reaction notes

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