Hydrochloric Acid → HCID 178448598, compound

HRID 2206444Notes

Reaction equation

HRID 2206444 reaction equation
[CH2:1]([NH2:5])[CH2:2][CH2:3][CH3:4].C=O.[ClH:8].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=O)=[CH:13][CH:12]=1.[C:25](=O)(O)[O-].[Na+]>C(#N)C.C(O)C>[Cl-:8].[CH2:1]([N:5]1[C:17]([C:14]2[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)=[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N+:20]2=[CH:25]1)[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 8007ButylamineHCID 80559(4-Methoxyphenyl)-2-pyridinylmethanoneHCID 516892Sodium Bicarbonate

Product 1

HCID 178448598HCID 178448598, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6342AcetonitrileSolvent

Procedure

was prepared according to general procedure (A, in which 35 μl n-butylamine (0.35 mmol, 1 equiv), 40 μl formalin (0.53 mmol, 1.5 equiv), 0.11 mL 3.14 M hydrochloric acid in ethanol (0.35 mmol, 1 equiv) and 76 mg (4-methoxyphenyl)(pyridin-2-yl)methanone (0.35 mmol, 1 equiv) were combined in 0.70 mL acetonitrile and maintained at room temperature for 12 hours. The crude material was then dissolved in 3 mL ethanol and stirred with sodium bicarbonate at room temperature for 10 min. The resulting suspension was then filtered through a 1.0 mL 0.2 um nylon syringe tip filter and the solid was rinsed with an additional 1 mL of ethanol. The combined filtrate was then concentrated and triturated with 2 mL diethyl ether. The resulting solid was filtered and rinsed with diethyl ether two times using 1 mL of diethyl ether for each rinse providing 0.10 g 2-butyl-1-(4-methoxyphenyl)-2H-imidazo[1,5-a]pyridin-4-ium chloride (0.23 mmol, a 66% yield) as a white solid.

Workup

  1. customwas prepared
  2. filtrationThe resulting suspension was then filtered through a 1.0 mL 0.2 um nylon syringe tip
  3. filtrationfilter
  4. washthe solid was rinsed with an additional 1 mL of ethanol
  5. concentrationThe combined filtrate was then concentrated
  6. customtriturated with 2 mL diethyl ether
  7. filtrationThe resulting solid was filtered
  8. washrinsed with diethyl ether two times

Sources & evidence

ORD record
ord-5d15f821677e4d50a7fe06335c9cc789
Source dataset
uspto-grants-2016_06
Patent number
US09371448B2

Reaction notes

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