Imidazole → HCID 9907008, compound

HRID 1645816Notes

Reaction equation

HRID 1645816 reaction equation
Cl.O[CH:3]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])[CH2:7][CH2:6]1.S(Cl)(Cl)=O.[NH:29]1[CH:33]=[CH:32][N:31]=[CH:30]1>CCOCC.CO.O>[CH3:18][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[N:8]1[CH2:9][CH2:10][N:5]([CH2:4][CH:3]([N:29]2[CH:33]=[CH:32][N:31]=[CH:30]2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:6][CH2:7]1

Participants

7

Reactant 3

HCID 795ImidazoleHCID 24386Thionyl ChlorideHCID 67749831HCID 67749831, compound

Product 1

HCID 9907008HCID 9907008, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1-(2-hydroxy-2-phenylethyl)-4-(2-methoxyphenyl) piperazine hydrochloride (1.6 g) and thionyl chloride (5 ml) was stirred at reflux for 5 min. The clear solution was then diluted with ether and the precipitated product collected by filtration and washed well with ether. The solid was added to a solution of imidazole (2.4 g, 40 mmol) in methanol (20 ml) and heated to reflux for 1 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed several times with water, dried (Na2SO4), and concentrated in vacuo. The residue was dissolved in ethanol (10 ml) and acidified with ethereal-HC1. Further addition of ether precipitated the hydrochloride (1.07 g, 55%), which was recrystallised from methanol-ethanol (20 ml; 1:3) to afford the title compound as the trihydrochloride 1.25 hydrate (0.54 g), m.p. 203°-204° C. (Found: C,53.2; H,6.4; N,11.2. C22H26N4O.3HC1.1.25 H2O requires C,53.4; H,6.4; N,11.3%).

Workup

  1. temperatureat reflux for 5 min
  2. filtrationthe precipitated product collected by filtration
  3. washwashed well with ether
  4. temperatureheated
  5. temperatureto reflux for 1 h
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed several times with water
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo
  10. dissolutionThe residue was dissolved in ethanol (10 ml)
  11. additionFurther addition of ether
  12. customprecipitated the hydrochloride (1.07 g, 55%), which
  13. customwas recrystallised from methanol-ethanol (20 ml; 1:3)

Sources & evidence

ORD record
ord-14d263ef60914b97ae1ef44620804cfc
Source dataset
uspto-grants-1993_01
Patent number
US05177078

Reaction notes

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