Toluene → 4-Benzyloxycarbonyl-1-[4-(4-pyridyl)benzyl]-2-piperazinone

HRID 1840535Notes

Reaction equation

HRID 1840535 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][C:21](Br)=[CH:20][CH:19]=2)[C:13](=[O:25])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:26]1[CH:31]=[CH:30][C:29](OB(O)O)=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>C(OCC)(=O)C.C(O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:29]3[CH:30]=[CH:31][N:26]=[CH:27][CH:28]=3)=[CH:20][CH:19]=2)[C:13](=[O:25])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 218058124-Pyridylboric acidHCID 23447549Benzyl 4-[(4-bromophenyl)methyl]-3-oxopiperazine-1-carboxylate

Product 1

HCID 234475764-Benzyloxycarbonyl-1-[4-(4-pyridyl)benzyl]-2-piperazinoneYield 40.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-benzyloxycarbonyl-1-(4-bromobenzyl)-2-piperazinone (807 mg), 4-pyridylboric acid (244 mg), tetrakis (triphenylphosphine)palladium (69 mg), 2M sodium carbonate solution (2 ml), toluene (8 ml) and ethanol (2 ml) was refluxed overnight. After the mixture was cooled, ethyl acetate was added to the reaction solution. The mixture was washed with water and saturated brine, dried (MgSO4) and concentrated. The residue was purified with silica gel column chromatography (ethyl acetate) to give colorless crystals of the title compound (283 mg).

Workup

  1. temperaturewas refluxed overnight
  2. temperatureAfter the mixture was cooled
  3. washThe mixture was washed with water and saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified with silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-6045df75ebf54ba3b4ee5e4747db18f6
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

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