1-Benzylpiperazine → HCID 68337899, compound

HRID 574246Notes

Reaction equation

HRID 574246 reaction equation
Br[C:2]1[C:3](=[O:22])[NH:4][C:5](=[O:21])[N:6]([CH2:9][C:10]2[C:15]([C:16]([F:19])([F:18])[F:17])=[CH:14][CH:13]=[CH:12][C:11]=2[F:20])[C:7]=1[CH3:8].[CH2:23]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(#N)C>[CH2:23]([N:30]1[CH2:35][CH2:34][N:33]([C:2]2[C:3](=[O:22])[NH:4][C:5](=[O:21])[N:6]([CH2:9][C:10]3[C:15]([C:16]([F:19])([F:18])[F:17])=[CH:14][CH:13]=[CH:12][C:11]=3[F:20])[C:7]=2[CH3:8])[CH2:32][CH2:31]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 759941-BenzylpiperazineHCID 116823865-Bromo-1-{[2-fluoro-6-(trifluoromethyl)phenyl]methyl}-6-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

Product 1

HCID 68337899HCID 68337899, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

5-bromo-1-(2-fluoro-6-trifluoromethyl-benzyl)-6-methyl-1H-pyrimidine-2,4-dione (1.50 g, 3.94 mmol), 1-benzyl-piperazine (5.5 mL, 31.5 mmol), and acetonitrile (1 mL) were placed in a microwave vessel and heated at 120° C. for 1.5 hr by microwave irradiation with stirring. Following concentration, the residue was purified using silica gel chromatography (eluent: hexane/ethyl acetate/dichloromethane, 1/2/1) and dried in a vacuum to afford the 1.48 g of the compound as a white solid (yield 79%). 1H NMR (300 MHz, CDCl3) δ 2.15 (2H, m), 2.31 (3H, s), 2.50 (2H, m), 2.78 (2H, m), 3.52 (3H, s), 3.58 (2H, m), 5.36 (2H, s), 7.19-7.41 (7H, m), 7.53 (1H, d)

Workup

  1. concentrationconcentration
  2. customthe residue was purified
  3. customdried in a vacuum

Sources & evidence

ORD record
ord-eb14a2533df248b7a1492cdaeeeafbd6
Source dataset
uspto-grants-2015_05
Patent number
US09034850B2

Reaction notes

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