Triethylamine → 4-(4-Methoxybenzyl)-3,3-dimethyl-piperazin-2-one

HRID 2391853Notes

Reaction equation

HRID 2391853 reaction equation
[CH3:1][C:2]1([CH3:9])[NH:7][CH2:6][CH2:5][NH:4][C:3]1=[O:8].[CH3:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Br)=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][N:7]2[CH2:6][CH2:5][NH:4][C:3](=[O:8])[C:2]2([CH3:9])[CH3:1])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1650214-Methoxybenzyl bromide2×HCID 2111572-Piperazinone, 3,3-dimethyl-

Product 1

HCID 669145564-(4-Methoxybenzyl)-3,3-dimethyl-piperazin-2-oneYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3,3-dimethyl-piperazin-2-one (Step 108.4) (3.7 g, 28.9 mmol), 4-methoxybenzyl bromide (5.4 mL, 37.6 mmol, 1.3 equiv) and triethylamine (5.2 mL, 37.6 mmol, 1.3 equiv) in DCM (60 mL) was stirred for 48 h at rt. Additional 5.0 mL of 4-methoxybenzyl bromide were added and the mixture was stirred for 72 h at rt, then concentrated. The residue was diluted with DCM/saturated aqueous solution of NaHCO3. The aqueous phase was separated and extracted with DCM. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The residue was triturated in DCM to provide 3.95 g of the title compound as a white solid: ESI-MS: 249.2 [M+H]+; TLC: Rf=0.16 (Hex/EtOAc, 2:3).

Workup

  1. stirringthe mixture was stirred for 72 h at rt
  2. concentrationconcentrated
  3. additionThe residue was diluted with DCM/saturated aqueous solution of NaHCO3
  4. customThe aqueous phase was separated
  5. extractionextracted with DCM
  6. washThe organic phase was washed with H2O and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was triturated in DCM

Sources & evidence

ORD record
ord-9e771121bcb24b59ae3a6bb3a564a9c1
Source dataset
uspto-grants-2012_09
Patent number
US08273882B2

Reaction notes

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