Dimethylamine → 7-[(1-benzyl-5-methyl-1H-imidazol-4-yl)methyl]-10-[(dimethylamino)methyl]-8,9-dihydropyrido[1,2-a]indol-6(7H)-one

HRID 486224Notes

Reaction equation

HRID 486224 reaction equation
[CH2:1]([N:8]1[C:12]([CH3:13])=[C:11]([CH2:14][CH:15]2[C:27](=[O:28])[N:19]3[C:20]4[C:25]([CH:26]=[C:18]3[CH2:17][CH2:16]2)=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:29][NH:30][CH3:31].[CH2:32]=O>C(O)(=O)C>[CH2:1]([N:8]1[C:12]([CH3:13])=[C:11]([CH2:14][CH:15]2[C:27](=[O:28])[N:19]3[C:20]4[C:25]([C:26]([CH2:29][N:30]([CH3:32])[CH3:31])=[C:18]3[CH2:17][CH2:16]2)=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 190973117-[(1-benzyl-5-methyl-1H-imidazol-4-yl)methyl]-8,9-dihydropyrido[1,2-a]indol-6(7H)-one

Product 1

HCID 190973047-[(1-benzyl-5-methyl-1H-imidazol-4-yl)methyl]-10-[(dimethylamino)methyl]-8,9-dihydropyrido[1,2-a]indol-6(7H)-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 7-[(1-benzyl-5-methyl-1H-imidazol-4-yl)methyl]-8,9-dihydropyrido[1,2-a]indol-6(7H)-one (451 mg) in acetic acid (2.5 ml) at 10° C. were added successively aqueous 50% dimethylamine solution (0.17 ml) and aqueous 35% formaldehyde solution (0.16 ml). The mixture was heated at 60° C. for 16 hours. After evaporation of the solvent, the residue was dissolved in water, made basic with aqueous 3N sodium hydroxide solution, and extracted twice with chloroform. The chloroform layer was washed with water and brine, dried over anhydrous sodium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography (methanol-chloroform) to give 7-[(1-benzyl-5-methyl-1H-imidazol-4-yl)methyl]-10-[(dimethylamino)methyl]-8,9-dihydropyrido[1,2-a]indol-6(7H)-one (233 mg) as an oil.

Workup

  1. customAfter evaporation of the solvent
  2. dissolutionthe residue was dissolved in water
  3. extractionextracted twice with chloroform
  4. washThe chloroform layer was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (methanol-chloroform)

Sources & evidence

ORD record
ord-97c0dcce96404826afb46ab5a8dc5d53
Source dataset
uspto-grants-1994_03
Patent number
US05290785

Reaction notes

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