Hydrogen Bromide → HCID 19038973, compound

HRID 1757584Notes

Reaction equation

HRID 1757584 reaction equation
[NH2:1][C:2]1[C:7]2[N:8]=[C:9]([CH2:16][CH2:17][CH2:18][CH3:19])[N:10]([CH2:11][C:12]([CH3:15])([CH3:14])O)[C:6]=2[C:5]([CH3:20])=[C:4]([CH3:21])[N:3]=1.Br.[ClH:23].CCOCC>CO>[ClH:23].[CH2:16]([C:9]1[N:10]([CH:11]=[C:12]([CH3:14])[CH3:15])[C:6]2[C:5]([CH3:20])=[C:4]([CH3:21])[N:3]=[C:2]([NH2:1])[C:7]=2[N:8]=1)[CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 10108297HCID 10108297, compound

Product 1

HCID 19038973HCID 19038973, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Amino-2-butyl-α,α,6,7-tetramethyl-1H-imidazo[4,5-c]pyridine-1-ethanol (about 200 mg) was combined with concentrated hydrobromic acid (50mL) and heated at reflux overnight. The reaction mixture was concentrated under vacuum. The residue was taken up in methanol then diluted with ether. The resulting precipitate was collected then partitioned between methylene chloride and 10% sodium hydroxide. The organic layer was separated, dried over magnesium sulfate then concentrated to provide an oil. The oil was taken up in methanol then combined with 0.05 mL of concentrated hydrochloric acid followed by dilution with ether. The resulting precipitate was collected, rinsed with ether and dried to provide 60 mg of the desired product as a white solid, m.p. 205° C.(dec.). Analysis: Calculated for C16H24N4 +1.6 HCl: % C, 58.10; % H, 7.80; % N, 16.94; Found: % C, 57.95; % H, 7.87; % N, 16.89.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. additionthen diluted with ether
  5. customThe resulting precipitate was collected
  6. customthen partitioned between methylene chloride and 10% sodium hydroxide
  7. customThe organic layer was separated
  8. dry with materialdried over magnesium sulfate
  9. concentrationthen concentrated
  10. customto provide an oil
  11. customThe resulting precipitate was collected
  12. washrinsed with ether
  13. customdried

Sources & evidence

ORD record
ord-5b6d0014d6bc45bd8e2361efddfc892b
Source dataset
uspto-grants-1995_08
Patent number
US05446153

Reaction notes

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