Potassium Hydroxide → HCID 67954505, compound

HRID 2088880Notes

Reaction equation

HRID 2088880 reaction equation
[CH2:1]([C:5]1[N:6]=[C:7]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[NH:8][CH:9]=1)[CH:2]([CH3:4])[CH3:3].[OH-].[K+].Cl.Cl[CH2:27][CH2:28][N:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1>CS(C)=O>[CH2:1]([C:5]1[N:6]=[C:7]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[CH2:12][CH2:11]2)[N:8]([CH2:27][CH2:28][N:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)[CH:9]=1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 178441349HCID 178441349, compound

Product 1

HCID 67954505HCID 67954505, compoundYield 106.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
45 °C

Procedure

Combine tert-butyl 4-(4-isobutyl-1H-imidazol-2-yl)piperidine-1-carboxylate (1.50 g, 4.88 mmol) and potassium hydroxide (1.65 g, 6.0 eq) (freshly powdered) in dimethyl sulfoxide (30 mL). Heat the reaction mixture to 45° C. under nitrogen. After 5 minutes, add 1-(2-chloroethyl)pyrrolidine hydrochloride (1.08 g, 1.3 eq). Stop heating after 2 hours. Add water and extract with ethyl acetate. Dry the organics over anhydrous magnesium sulfate, filter, and concentrate in vacuo to give the title compound as a yellow oil (2.11 g, 100%). MS (ES) m/z=405 [M]+.

Workup

  1. temperatureStop heating after 2 hours
  2. extractionAdd water and extract with ethyl acetate
  3. dry with materialDry the organics over anhydrous magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-6621be077f824260b36621086ee58da1
Source dataset
uspto-grants-2013_05
Patent number
US08436002B2

Reaction notes

Loading…