Formaldehyde → HCID 19423570, compound

HRID 743064Notes

Reaction equation

HRID 743064 reaction equation
N[C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][CH:31]=1)[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([N:12]2[CH:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]2=[O:28])[CH2:8][CH2:7]1.[CH2:32]=O.[C:34]([BH3-])#[N:35].[Na+]>CO>[CH3:32][N:35]([CH3:34])[C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][CH:31]=1)[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([N:12]2[CH:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]2=[O:28])[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 19423607HCID 19423607, compound

Product 1

HCID 19423570HCID 19423570, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 200 mg (0.48 mmol) of 3-[1-(3-aminobenzyl)piperidin-4-yl]-4-phenyl-3,4-dihydro-2(1H)quinazolinone in 20 mL of methanol were added 415 mg (4.85 mmol) of formaldehyde and 243 mg (3.88 mmol) of sodium cyanoborohydride and the mixture was stirred for 12 hours at ambient temperature. Then, 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 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, 1:9:90 aqueous ammonia:methanol:chloroform) to give 210 mg (0.47 mmol) of the title compound.

Workup

  1. concentrationThen, the reaction mixture was concentrated in vacuo
  2. additionThe residue was diluted with water
  3. extractionextracted with chloroform
  4. customThe organic layer separated
  5. customwas dried on potassium carbonate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by means of column chromatography (silica gel, 1:9:90 aqueous ammonia:methanol:chloroform)

Sources & evidence

ORD record
ord-c3f41d56fba7453d847ab7c4402824af
Source dataset
uspto-grants-1996_09
Patent number
US05556860

Reaction notes

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