Methyl iodide → Ethyl 1,4-dibenzyl-2-methylpiperazine-2-carboxylate

HRID 502526

반응식

HRID 502526 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH:9]1[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[CH3:27]C([N-]C(C)C)C.CI>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:10][C:9]1([CH3:27])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 2736402Ethyl 1,4-dibenzylpiperazine-2-carboxylate

생성물 1

HCID 58855869Ethyl 1,4-dibenzyl-2-methylpiperazine-2-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To ethyl 1,4-dibenzylpiperazine-2-carboxylate (35.4 g, 0.1 mol) in THF(200 mL) cooled to −78° C. was added dropwise LDA (64 mL, 1.8 M). The reaction was stirred at −78° C. for 1 h then MeI (7.2 mL, 0.11 mol) was added. The reaction was allowed to slowly warm to RT then quenched with sat'd NH4Cl. Water (200 mL) was added and the residue was extracted with EtOAc (200 mL). The EtOAc layer was washed twice with water then the solvent was removed in vacuo. Silica gel chromatography provided ethyl 1,4-dibenzyl-2-methylpiperazine-2-carboxylate (compound 10A) 14.91 g. HPLC RT: 2.42 min (Chromolith SpeedROD 4.6×50 mm, 10-90% aqueous MeOH over 4 minutes containing 0.1% TFA, 4 ml/min, monitoring at 220 nm). (M+H)+:353.

후처리

  1. temperatureto slowly warm to RT
  2. customthen quenched with sat'd NH4Cl
  3. additionWater (200 mL) was added
  4. extractionthe residue was extracted with EtOAc (200 mL)
  5. washThe EtOAc layer was washed twice with water
  6. customthe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-9752f1828ec54e8483a9493af4f20d3d
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776859B2

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