Furfural → HCID 19423616, compound

HRID 743062Notes

Reaction equation

HRID 743062 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([N:8]2[CH:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]2=[O:24])[CH2:4][CH2:3]1.[CH:25](=O)[C:26]1[O:30][CH:29]=[CH:28][CH:27]=1.C([BH3-])#N.[Na+]>CO>[O:30]1[CH:29]=[CH:28][CH:27]=[C:26]1[CH2:25][N:2]1[CH2:3][CH2:4][CH:5]([N:8]2[CH:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]2=[O:24])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 7362FurfuralHCID 5003444Sodium cyanoborohydrideHCID 67627664HCID 67627664, compound

Product 1

HCID 19423616HCID 19423616, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 344 mg (1.0 mmol) of 3-(piperidin-4-yl)-4-phenyl-3,4-dihydro-2(1H)-quinazolinone HCl salt and 384 mg (4.0 mmol) of furfural in 40 mL of methanol was added 123 mg (2.0 mmol) of sodium cyano-borohydride under ice-cooling. After being stirred for 12 hours at ambient temperature, the reaction mixture was concentrated in vacuo. The residue was diluted with water, and the mixture was adjusted to pH 10 with aqueous ammonia, and then extracted with chloroform. The organic layer separated was dried on potassium carbonate and then concentrated in vacuo. The residue was purified by means of column chromatography (silica gel, 1:9 methanol:chloroform) to give 329 mg (0.85 mmol) of the title compound.

Workup

  1. temperaturecooling
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. additionThe residue was diluted with water
  4. extractionextracted with chloroform
  5. customThe organic layer separated
  6. customwas dried on potassium carbonate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by means of column chromatography (silica gel, 1:9 methanol:chloroform)

Sources & evidence

ORD record
ord-0415daccd5244dd9bec35b5a5cfac36e
Source dataset
uspto-grants-1996_09
Patent number
US05556860

Reaction notes

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