Benzyl Bromide → (3r,5s)-1-Benzyl-3,5-dimethylpiperazine

HRID 500446ノート

反応式

HRID 500446 の反応式
[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][C@@H:4]([CH3:8])[NH:3]1.C(=O)(O)[O-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[CH2:14]([N:6]1[CH2:5][C@H:4]([CH3:8])[NH:3][C@H:2]([CH3:1])[CH2:7]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 516892Sodium BicarbonateHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazine

生成物 1

HCID 12197174(3r,5s)-1-Benzyl-3,5-dimethylpiperazine収率 51.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (cis)-2,6-dimethylpiperazine (900 mg, 8.49 mmol) and sodium bicarbonate (0.2 ml of saturated solution) in THF (5 ml) was added benzyl bromide (1.02 ml, 8.49 mmol). The mixture was exposed to microwave irradiation at 80° C. for 15 minutes. The solvent was removed in vacuo and the residue was washed with sodium bicarbonate solution and extracted with dichloromethane. The residue was purified by flash chromatography eluting with 5-10% (v/v) methanol in dichloro-methane to afford 1-N-benzyl-(cis)-3,5-dimethylpiperazine as a clear oil (900 mg, 4.40 mmol).

後処理

  1. customirradiation at 80° C. for 15 minutes
  2. customThe solvent was removed in vacuo
  3. washthe residue was washed with sodium bicarbonate solution
  4. extractionextracted with dichloromethane
  5. customThe residue was purified by flash chromatography
  6. washeluting with 5-10% (v/v) methanol in dichloro-methane

出典と根拠

ORDレコード
ord-0831377fd2064077964211892e15656a
出典データセット
uspto-grants-2010_08
特許番号
US07772227B2

反応ノート

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