Hydrochloric Acid → 5-(p-Tolyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine hydrochloride

HRID 477981Notes

Reaction equation

HRID 477981 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]3[CH:15]=[N:16][CH:17]=[C:13]3[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[H][H].[ClH:20]>C(O)C.[Pd]>[ClH:20].[C:3]1([CH3:2])[CH:8]=[CH:7][C:6]([CH:9]2[N:14]3[CH:15]=[N:16][CH:17]=[C:13]3[CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 136494325-(p-Hydroxymethylphenyl)imidazo[1,5-a]pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 136882175-(p-Tolyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 0.36 g of 5-(p-hydroxymethylphenyl)imidazo[1,5-a]pyridine in 25 ml of ethanol and 6.4 ml of concentrated hydrochloric acid is hydrogenated with 0.15 g 10% palladium on charcoal at 40 psi of hydrogen and 60° for 4 h. The reaction mixture is filtered and evaporated and the residue is partitioned between methylene chloride and sodium bicarbonate solution. The organic phase is dried over sodium sulfate and evaporated to an oil which is purified by preparative layer chromatography on silica with ethyl acetate. The hydrochloride salt is prepared in acetone with 1.1 molar equivalents of ethereal hydrogen chloride to yield the title compound, m.p. 173°-175°.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customevaporated
  3. customthe residue is partitioned between methylene chloride and sodium bicarbonate solution
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customevaporated to an oil which
  6. customis purified by preparative layer chromatography on silica with ethyl acetate

Sources & evidence

ORD record
ord-756d92b9c8c7470c8eb229caccb85d1d
Source dataset
uspto-grants-1989_12
Patent number
US04889861

Reaction notes

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