Piperazine → 1-Benzyl-2-oxo-4-piperazin-1-yl-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile

HRID 901234Notes

Reaction equation

HRID 901234 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][N:16]=2)[C:11](Cl)=[C:10]([C:19]#[N:20])[C:9]1=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>ClCCl>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][N:16]=2)[C:11]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[C:10]([C:19]#[N:20])[C:9]1=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 596995491-Benzyl-4-chloro-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile

Product 1

HCID 596995621-Benzyl-2-oxo-4-piperazin-1-yl-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrileYield 98.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 1-benzyl-4-chloro-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile (8) (530 mg, 1.79 mmol) in dichloromethane was added slowly to a stirred solution of piperazine (463 mg, 5.37 mmol) in dichloromethane at room temperature. The solution was further stirred overnight at room temperature and diluted by dichloromethane. The solution was subsequently washed with saturated NaHCO3 solution, water and brine, then dried over Na2SO4 and evaporated to yield 610 mg (98%) of 1-benzyl-2-oxo-4-piperazin-1-yl-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile (9) as white solids. MP: 211° C.; 1H-NMR (DMSO-d6): δ 2.93 (m, 4H), 3.57 (m, 4H), 5.53 (s, 2H), 7.20-7.27 (m, 5H), 7.34 (dd, J=4.8, 8.0 Hz, 1H), 8.26 (dd, J=1.6, 8.0 Hz, 1H), 8.65 (dd, J=1.6, 8.0 Hz, 1H); EIMS: 296 (M+1). EIMS: 346 (M+1).

Workup

  1. washThe solution was subsequently washed with saturated NaHCO3 solution, water and brine
  2. dry with materialdried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-1fd9436d204344f49048a5fb8f98618f
Source dataset
uspto-grants-2008_04
Patent number
US07361760B2

Reaction notes

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