Sodium Carbonate → HCID 178419891, compound

HRID 748654Notes

Reaction equation

HRID 748654 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.Cl.O[CH2:13][C:14]1[N:15]=[CH:16][NH:17][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>O.O1CCOCC1>[NH:17]1[CH:18]=[C:14]([CH2:13][N:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4][CH2:3][CH2:2]2)[N:15]=[CH:16]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 694601,2,3,4-Tetrahydroquinoline2×HCID 178418488HCID 178418488, compound

Product 1

HCID 178419891HCID 178419891, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1,2,3,4-tetrahydro-quinoline (Intermediate F1) (Commercially available from Aldrich) (1.62 mL, 12.6 mmol) and 4-hydroxymethyl-imidazole hydrochloride salt (commercially available from Aldrich) (Intermediate F2) (0.70 g, 5.1 mmol) and sodium carbonate (1.6 g, 15.1 mmol) in water (20 mL) and dioxane (10 mL) were heated at reflux for 24 h. The mixture was cooled to rt and extracted with ethyl acetate. The organic solution was dried over MgSO4, filtered and freed of solvent. The resultant oil was purified by chromatography on silica gel with 5% NH3-MeOH: dichloromethane to give 1-(1H-imidazol-4-ylmethyl)-1,2,3,4-tetrahydro-quinoline (Intermediate F3) as a solid, 0.54 g (50%).

Workup

  1. temperaturewere heated
  2. temperatureat reflux for 24 h
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic solution was dried over MgSO4
  5. filtrationfiltered
  6. customThe resultant oil was purified by chromatography on silica gel with 5% NH3-MeOH

Sources & evidence

ORD record
ord-7747a5d92aab4a79907be7918529bf1d
Source dataset
uspto-grants-2008_07
Patent number
US07399868B2

Reaction notes

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