Formaldehyde → 3-(1-Benzylpiperidin-4-yl)-1,3-dihydroimidazo[4,5-c]quinolin-2-one

HRID 1699253Notes

Reaction equation

HRID 1699253 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:9][C:10](=[O:26])[N:11]([CH:13]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:15][CH2:14]2)[CH:12]=1.[CH2:27]=O>C(Cl)(Cl)Cl>[C:20]1([CH2:19][N:16]2[CH2:17][CH2:18][CH:13]([N:11]3[C:12]4[CH:27]=[N:1][C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=5[C:8]=4[NH:9][C:10]3=[O:26])[CH2:14][CH2:15]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 18321264HCID 18321264, compound

Product 1

HCID 183215963-(1-Benzylpiperidin-4-yl)-1,3-dihydroimidazo[4,5-c]quinolin-2-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 2.67 g (7.66 mmol) of 4-(2-aminophenyl)-1,3-dihydro-1-[1-(phenylmethyl)-4-piperidinyl]-2H-imidazol-2-one in 50 ml of chloroform was mixed with 3.0 g of paraformaldehyde and refluxed for 3.5 hours. The residue remaining after evaporation of the solvent was taken up in 100 ml of methanol and acidified with methanolic hydrogen chloride solution. After stirring for one hour at room temperature the mixture was poured into 300 ml of saturated sodium hydrogen carbonate solution. The resulting mixture was extracted thoroughly with ethyl acetate, the combined extracts were dried over sodium sulphate and evaporated down in vacuo. The residue was purified by column chromatography over silica gel using FM4 as eluant. From the appropriate fractions 0.5 g (18.2% of theory) of a colourless, amorphous substance were isolated, Rf=0.24 (FM4)

Workup

  1. temperaturerefluxed for 3.5 hours
  2. customafter evaporation of the solvent
  3. additionwas poured into 300 ml of saturated sodium hydrogen carbonate solution
  4. extractionThe resulting mixture was extracted thoroughly with ethyl acetate
  5. dry with materialthe combined extracts were dried over sodium sulphate
  6. customevaporated down in vacuo
  7. customThe residue was purified by column chromatography over silica gel using FM4 as eluant
  8. customFrom the appropriate fractions 0.5 g (18.2% of theory) of a colourless, amorphous substance were isolated

Sources & evidence

ORD record
ord-3cbae0576d7a4efa8d5079086810dc4d
Source dataset
uspto-grants-2002_02
Patent number
US06344449B1

Reaction notes

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