Dimethylamine → pyrido[1,2-a]indol-6(7H)-one

HRID 486223Notes

Reaction equation

HRID 486223 reaction equation
CNC.C=O.CC1NC=NC=1C[CH:13]1[C:25](=[O:26])[N:17]2[C:18]3[C:23]([CH:24]=[C:16]2[CH2:15][CH2:14]1)=[CH:22][CH:21]=[CH:20][CH:19]=3>C(O)(=O)C>[CH:22]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:23]=1[CH:24]=[C:16]1[CH:15]=[CH:14][CH2:13][C:25](=[O:26])[N:17]12

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 102656158,9-dihydro-7-[(5-methyl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one

Product 1

HCID 17893253pyrido[1,2-a]indol-6(7H)-oneYield 87.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of aqueous 50% dimethylamine solution (0.20 ml), aqueous 35% formaldehyde solution (0.20 ml), and acetic acid (4 ml) at 15° C. was added 8,9-dihydro-7-[(5-methyl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one (418 mg). The mixture was heated at 60°]C. for 24 hours. After evaporation of the solvent, the residue was dissolved in water, made basic with aqueous 3N sodium hydroxide solution, and extracted three times with chloroform. The chloroform layer was washed with water and brine, dried over anhydrous sodium sulfate, and evaporated in vacuo. The oil was purified by silica gel column chromatography (20% methanol-chloroform) to give 8,9-dihydro-10-[(dimethylamino)methyl]-7-(5-methyl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one (240 mg).

Workup

  1. temperatureThe mixture was heated at 60°]C
  2. customAfter evaporation of the solvent
  3. dissolutionthe residue was dissolved in water
  4. extractionextracted three times with chloroform
  5. washThe chloroform layer was washed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated in vacuo
  8. customThe oil was purified by silica gel column chromatography (20% methanol-chloroform)

Sources & evidence

ORD record
ord-a068f6fad92f43c2968b7172336dde63
Source dataset
uspto-grants-1994_03
Patent number
US05290785

Reaction notes

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