Cyanamide → 2-Amino-4-(1-benzoyl-4-piperidinyl)quinazoline

HRID 617176Notes

Reaction equation

HRID 617176 reaction equation
Cl.[C:2]([N:10]1[CH2:15][CH2:14][CH:13]([C:16](=O)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[NH2:23])[CH2:12][CH2:11]1)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[N:25]#[C:26][NH2:27].C(=O)([O-])O.[Na+]>O>[NH2:27][C:26]1[N:25]=[C:16]([CH:13]2[CH2:14][CH2:15][N:10]([C:2](=[O:9])[C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)[CH2:11][CH2:12]2)[C:17]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:23]=1

Participants

5

Reactant 3

HCID 9864CyanamideHCID 516892Sodium BicarbonateHCID 218515361-Benzoyl-4-(2-aminobenzoyl)piperidine hydrochloride

Product 1

HCID 154287732-Amino-4-(1-benzoyl-4-piperidinyl)quinazolineYield 97.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The titled compound was prepared by warming a mixture of 1-benzoyl-4-(2-aminobenzoyl)piperidine hydrochloride (17 g, 0.049 mol) and cyanamide (4.12 g, 0.098 mol). At about 50° C., vigorous exothermic reaction occurred. After the reaction was finished, the reaction mixture was cooled, water was added to the reaction mixture, and then added sodium hydrogencarbonate to make the mixture basic. The mixture was then extracted with dichloromethane. The organic layer was washed with aqueous solution of saturated sodium chloride, and then dried over sodium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give the titled compound (15.9 g) as a foam.

Workup

  1. customThe titled compound was prepared
  2. temperatureby warming
  3. customAt about 50° C., vigorous exothermic reaction
  4. temperaturethe reaction mixture was cooled
  5. extractionThe mixture was then extracted with dichloromethane
  6. washThe organic layer was washed with aqueous solution of saturated sodium chloride
  7. dry with materialdried over sodium sulfate
  8. customevaporated in vacuo
  9. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-ad93f7913dc0453ea8fa2a3fb0472d06
Source dataset
uspto-grants-1999_09
Patent number
US05948786

Reaction notes

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