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

HRID 43139

반응식

HRID 43139 반응식
[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

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 1650214-Methoxybenzyl bromide2회HCID 2111572-Piperazinone, 3,3-dimethyl-

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7b7a491c70364dd0b9a78595a9ed8db0
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536175B2

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