1-Aminohomopiperidine → 10-(hexahydro-1H-azepin-1-yl)-2,10-dihydroimidazo[2,1-b]quinazolin-5(3H)-one

HRID 2350854Notes

Reaction equation

HRID 2350854 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[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>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)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 221981-AminohomopiperidineHCID 32369051-(2-Fluorobenzoyl)-2-methylthio-2-imidazoline

Product 1

HCID 1438711910-(hexahydro-1H-azepin-1-yl)-2,10-dihydroimidazo[2,1-b]quinazolin-5(3H)-oneYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 10.0 g (42.0 mmoles) of the product of Example 1 in 50 ml of N-amino-homopiperidine was heated at reflux for 10 minutes. Upon cooling, a white, crystalline solid formed. The mixture was diluted with water (100 ml) and the solid was collected, washed with water, and air-dried to give 9.03 g of 10-(hexahydro-1H-azepin-1-yl)-2,10-dihydroimidazo[2,1-b]quinazolin-5(3H)-one. Melting point 206°-208° C. Total yield 76%.

Workup

  1. temperatureat reflux for 10 minutes
  2. temperatureUpon cooling
  3. customa white, crystalline solid formed
  4. customthe solid was collected
  5. washwashed with water
  6. customair-dried

Sources & evidence

ORD record
ord-bf592546447d4598b14378d415fb21a7
Source dataset
uspto-grants-1989_10
Patent number
US04871732

Reaction notes

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