Triethylamine → 4-Benzylpiperazine-2,6-dione

HRID 271621

反応式

HRID 271621 の反応式
[CH2:1]([N:8]([CH2:13][C:14]([OH:16])=O)[CH2:9][C:10](O)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:19](CC)CC)C.FC(F)(F)C(N)=O.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[CH2:1]([N:8]1[CH2:13][C:14](=[O:16])[NH:19][C:10](=[O:11])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 67717TrifluoroacetamideHCID 77606N-Benzylaminodiacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

生成物 1

HCID 5609674-Benzylpiperazine-2,6-dione収率 73.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a suspensiopn of 15 g (67 mmoles) of benzyliminodiacetic acid in 300 ml of CH2Cl2, 28 ml (201 mmoles) of triethylamine, 21.77 g (161 mmoles) of 1H-hydroxybenztriazole and 10.6 g (94 mmoles) of trifluoroacetamide are successively added and then 28.34 g (147.8 mmoles) of 1-[3(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride is added at 0° C. The reaction mixture is allowed to warm to ambient temperature and stirred for 18 hours. The reaction mixture is quenched with cold H2O and extracted with CH2Cl2. The combined extracts are washed with H2O brine, dried over MgSO4 and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: n-Hexane:AcOEt=2:1) to give 10 g of desired 4-benzyl-piperazine-2,6-dione in 73% yield.

後処理

  1. customThe reaction mixture is quenched with cold H2O
  2. extractionextracted with CH2Cl2
  3. washThe combined extracts are washed with H2O brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by silica gel column chromatography (eluent: n-Hexane:AcOEt=2:1)

出典と根拠

ORDレコード
ord-220d3626754144a89a260336a6c2e2a7
出典データセット
uspto-grants-2008_11
特許番号
US07452886B2

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