1-Aminopiperidine → 2,10-dihydro-10-(1-piperidinyl)imidazo[1,2-a]pyrido[2,3-d]pyrimidin-5(3H)-one

HRID 2350859Notes

Reaction equation

HRID 2350859 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[CH2:23][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)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

3

Reactant 2

HCID 166581-AminopiperidineHCID 143871351-(2-Chloropyridine-3-carbonyl)-2-methylthio-2-imidazoline

Product 1

HCID 143871372,10-dihydro-10-(1-piperidinyl)imidazo[1,2-a]pyrido[2,3-d]pyrimidin-5(3H)-oneYield 54.1%

Conditions

Temperature
160 °C

Procedure

A mixture of 10.0 g (39.1 mmoles) of the product of Example 12 and 11.4 g (0.1114 mole) of 1-aminopiperidine was heated at 160° C. for 1 hour. The mixture was concentrated by Kugelrohr distillation and the residue was partitioned between methylene chloride and water. The organic layer was dried (sodium sulfate) and concentrated to a small volume. The resulting crystals were collected to give 5.74 g of 2,10-dihydro-10-(1-piperidinyl)imidazo[1,2-a]pyrido[2,3-d]pyrimidin-5(3H)-one. Melting point 206°-207° C. Total yield 54%.

Workup

  1. concentrationThe mixture was concentrated 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 to a small volume
  5. customThe resulting crystals were collected

Sources & evidence

ORD record
ord-eba6304544474dc7a7995d835908d775
Source dataset
uspto-grants-1989_10
Patent number
US04871732

Reaction notes

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