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

HRID 43139

反応式

HRID 43139 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7b7a491c70364dd0b9a78595a9ed8db0
出典データセット
uspto-grants-2013_09
特許番号
US08536175B2

関連ノート

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