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

HRID 500446노트

반응식

HRID 500446 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0831377fd2064077964211892e15656a
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772227B2

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