1-Aminopiperidine → 2,10-dihydro-10-(1-piperidinyl)imidazo[2,1-b]quinazolin-5(3H)-one

HRID 2350853Notes

Reaction equation

HRID 2350853 reaction equation
F[C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([N:6]1[CH2:10][CH2:9][N:8]=[C:7]1SC)=[O:5].[NH2:17][N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>COCCOCCOC.O>[N:18]1([N:17]2[C:2]3[C:3](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:4](=[O:5])[N:6]3[CH2:10][CH2:9][N:8]=[C:7]23)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 2

HCID 166581-AminopiperidineHCID 32369051-(2-Fluorobenzoyl)-2-methylthio-2-imidazoline

Product 1

HCID 143871182,10-dihydro-10-(1-piperidinyl)imidazo[2,1-b]quinazolin-5(3H)-oneYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8150DiglymeSolvent

Procedure

A solution of 10.0 g (42.0 mmoles) of the product of Example 1 and 25 ml of 1-aminopiperidine in 50 ml of 2-methoxyethyl ether (diglyme) was heated at reflux for 15 hours. The solution as diluted while hot with about 5 ml of water and allowed to cool. The resulting white needles were collected, washed with ethanol, and air-dried to give 8.10 g of 2,10-dihydro-10-(1-piperidinyl)imidazo[2,1-b]quinazolin-5(3H)-one. Melting point 229°-231° C. Total yield 71%.

Workup

  1. temperatureat reflux for 15 hours
  2. temperatureto cool
  3. customThe resulting white needles were collected
  4. washwashed with ethanol
  5. customair-dried

Sources & evidence

ORD record
ord-a103d892249649af848becb865255592
Source dataset
uspto-grants-1989_10
Patent number
US04871732

Reaction notes

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