4-Cyanobenzaldehyde → HCID 9932025, compound

HRID 479458Notes

Reaction equation

HRID 479458 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[CH:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]2=[O:23])[CH2:3][CH2:2]1.Cl.O1CCOCC1.[C:31]([C:33]1[CH:40]=[CH:39][C:36]([CH:37]=O)=[CH:35][CH:34]=1)#[N:32].C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CO>[C:31]([C:33]1[CH:40]=[CH:39][C:36]([CH2:37][N:1]2[CH2:2][CH2:3][CH:4]([N:7]3[CH:16]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[NH:9][C:8]3=[O:23])[CH2:5][CH2:6]2)=[CH:35][CH:34]=1)#[N:32]

Participants

7

Reactant 5

HCID 660424-CyanobenzaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 15896329HCID 15896329, compoundHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 9932025HCID 9932025, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 100 mg (0.32 mmol) of 3-(piperidin-4-yl)-4-phenyl-3,4-dihydro-2(1H)-quinazolinone in 3 ml of methanol, 0.08 ml (0.32 mmol) of 4N hydrochloric acid/dioxane, 170 mg (1.3 mmol) of 4-cyanobenzaldehyde, 82 mg (1.3 mmol) of sodium cyanoborohydride were added subsequently under ice-cooling, and stirred at room temperature for 10 hours. Saturated aqueous sodium bicarbonate solution was added to the reaction mixture, followed by extracting with ethyl acetate, washing with water and saturated brine, and drying over anhydrous sodium sulfate. After the solvent was evaporated under reduced pressure, the obtained residue was purified by silica gel column chromatography (chloroform—2% methanol/chloroform) to give the title compound as colorless oil.

Workup

  1. temperaturecooling
  2. extractionby extracting with ethyl acetate
  3. washwashing with water and saturated brine
  4. dry with materialdrying over anhydrous sodium sulfate
  5. customAfter the solvent was evaporated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (chloroform—2% methanol/chloroform)

Sources & evidence

ORD record
ord-39a7884d4c864ed7ac2bfac7dd2c47e9
Source dataset
uspto-grants-2003_11
Patent number
US06645971B1

Reaction notes

Loading…