Ethanol → 8-Benzyloxy-3-dimethylaminoethyl-2-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

HRID 544465Notes

Reaction equation

HRID 544465 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][CH2:12][N:11]2[CH:15]=[C:16]([CH3:18])[N:17]=[C:10]12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:20][NH:21][CH3:22].C=O.[CH2:25](O)[CH3:26]>>[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][CH2:12][N:11]2[C:15]([CH2:26][CH2:25][N:21]([CH3:22])[CH3:20])=[C:16]([CH3:18])[N:17]=[C:10]12)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 139003398-Benzyloxy-2-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

Product 1

HCID 544310968-Benzyloxy-3-dimethylaminoethyl-2-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

Procedure

A mixture consisting of the product of Example 20 (1.52 g), dimethylamine hydrochloride (565 mg), paraformaldehyde (238 mg) and ethanol (10 ml) was refluxed for four hrs. After cooling to room temperature, the solvent was evaporated under reduced pressure. The residue was dissolved in chloroform, the solution washed four times with 5% aqueous potassium carbonate, dried over Na2SO4 and then the solvent was evaporated on a rotary evaporator. The residue was chromatographed on silica gel, eluting with acetone, to obtain the title compound (m.p. 68°-70° C.).

Workup

  1. temperaturewas refluxed for four hrs
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in chloroform
  4. washthe solution washed four times with 5% aqueous potassium carbonate
  5. dry with materialdried over Na2SO4
  6. customthe solvent was evaporated on a rotary evaporator
  7. customThe residue was chromatographed on silica gel
  8. washeluting with acetone

Sources & evidence

ORD record
ord-021ba16a21634f3dbd1cb3d6908f5b92
Source dataset
uspto-grants-1984_05
Patent number
US04450164

Reaction notes

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