Potassium Carbonate → HCID 178457131, compound

HRID 1733498Notes

Reaction equation

HRID 1733498 reaction equation
Cl.Cl.[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH2:11][CH2:12][NH:13][CH2:14][CH2:15][C:16]2[N:17]=[CH:18][NH:19][CH:20]=2)[CH:8]=[CH:9][CH:10]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:28][CH2:29][CH3:30]>CC(C)=O>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH2:11][CH2:12][N:13]([CH2:28][CH2:29][CH3:30])[CH2:14][CH2:15][C:16]2[N:17]=[CH:18][NH:19][CH:20]=2)[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 178490147HCID 178490147, compound

Product 1

HCID 178457131HCID 178457131, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred mixture of 3.2 g of the product of Step B, 5.1 g of potassium carbonate, 3.4 g of 1-iodopropane and 64 ml of acetone was refluxed under an inert atmosphere for 19 hours and the acetone was evaporated. 100 ml of water and 2 ml of sodium hydroxide were added to the mixture which was then extracted 3 times with 50 ml of methylene chloride. The combined organic phases were washed with 100 ml of water, dried over magnesium sulfate and filtered. The filtrate was evaporated to dryness and the 3.6 g of oil residue were chromatographed over silica gel to obtain 900 mg of N-[2-(3-methoxyphenyl)-ethyl]-N-propyl-1H-imidazol-4-ethanamine in the form of a yellow oil which was used as is for the next step. C.C.M. over silica (7-3 CHCl3 -Methanol): Rf=0.20.

Workup

  1. temperaturewas refluxed under an inert atmosphere for 19 hours
  2. customthe acetone was evaporated
  3. addition100 ml of water and 2 ml of sodium hydroxide were added to the mixture which
  4. extractionwas then extracted 3 times with 50 ml of methylene chloride
  5. washThe combined organic phases were washed with 100 ml of water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness
  9. customthe 3.6 g of oil residue were chromatographed over silica gel

Sources & evidence

ORD record
ord-e5166be23e1f4b71afc27bf90b29dd28
Source dataset
uspto-grants-1980_12
Patent number
US04242355

Reaction notes

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