1-Aminohomopiperidine → 10-(hexahydro-1H-azepin-1yl)-2,10-dihydroimidazo[1,2-a]pyrido[2,3-d]pyrimidin-5(3H)-one

HRID 2350860Notes

Reaction equation

HRID 2350860 reaction equation
Cl[C:2]1[C:7]([C:8]([N:10]2[CH2:14][CH2:13][N:12]=[C:11]2SC)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:17][N:18]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>>[N:18]1([N:17]2[C:2]3[N:3]=[CH:4][CH:5]=[CH:6][C:7]=3[C:8](=[O:9])[N:10]3[CH2:14][CH2:13][N:12]=[C:11]23)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

3

Reactant 2

HCID 221981-AminohomopiperidineHCID 143871351-(2-Chloropyridine-3-carbonyl)-2-methylthio-2-imidazoline

Product 1

HCID 1438713810-(hexahydro-1H-azepin-1yl)-2,10-dihydroimidazo[1,2-a]pyrido[2,3-d]pyrimidin-5(3H)-oneYield 66.3%

Conditions

Temperature
160 °C

Procedure

A mixture of 10.0 g (39.1 mmoles) of the product of Example 12 and 12.5 g (0.109 mole) of N-aminohomopiperidine was heated at 160° C. for 1 hour. Excess N-aminohomopiperidine was removed by Kugelrohr distillation and the residue was partitioned between methylene chloride and water. The organic layer was dried (sodium sulfate) and concentrated leaving 7.40 g of 10-(hexahydro-1H-azepin-1yl)-2,10-dihydroimidazo[1,2-a]pyrido[2,3-d]pyrimidin-5(3H)-one; melting point 217°-219° C. Total yield 66%.

Workup

  1. customExcess N-aminohomopiperidine was removed by Kugelrohr distillation
  2. customthe residue was partitioned between methylene chloride and water
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-859f62a318fa40cd854cf54ffaa69ebb
Source dataset
uspto-grants-1989_10
Patent number
US04871732

Reaction notes

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