Methyl iodide → Tert-butyl 4-{2-[methyl(methylsulfonyl)amino]phenyl}piperazine-carboxylate

HRID 228095노트

반응식

HRID 228095 반응식
[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)(=[O:4])=[O:3].[H-].[Na+].I[CH3:28]>CN(C=O)C.CCOC(C)=O>[CH3:28][N:5]([S:2]([CH3:1])(=[O:3])=[O:4])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17]1

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21935212Tert-Butyl 4-(2-[(Methylsulfonyl)Amino]Phenyl)-Piperazinecarboxylate

생성물 1

HCID 21935145Tert-butyl 4-{2-[methyl(methylsulfonyl)amino]phenyl}piperazine-carboxylate수율 97.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

실험 절차

In a 100 mL round bottomed flask equipped with magnetic stirring was added tert-butyl 4-{2-[(methylsulfonyl)-amino]phenyl}-piperazinecarboxylate (Preparation III) (692 mg, 1.947 mmol) and DMF (5 mL). After stirring 5 min, NaH (60% oil dispersion) (100 mg, 2.5 mmol) (Aldrich) in DMF (10 mL) was added. The reaction was stirred 20 min, then iodomethane (190 μl, 3.05 mmol) (Aldrich) was added via syringe. After stirring 2.5 h, the reaction was diluted with 150 mL EtOAc and washed 75 mL each, satd NH4C1, H2O, 10% NaHCO3 and brine. The organic layer was separated, dried over Na2SO4, filtered and concentrated in vacuo to give tert-butyl 4-{2-[methyl(methylsulfonyl)amino]phenyl}piperazine-carboxylate (700 mg). MS (ESI, pos. ion) m/z: 370 (M+H), (ESI, neg. ion) m/z: 368 (M−H). Calc'd for C17H27N3O4S: 369.48.

후처리

  1. customIn a 100 mL round bottomed flask equipped
  2. stirringAfter stirring 5 min
  3. stirringThe reaction was stirred 20 min
  4. stirringAfter stirring 2.5 h
  5. washwashed 75 mL each
  6. customThe organic layer was separated
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-22096a7aed7b46bc93c0c3d7d1b183e4
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560460B2

반응 노트

불러오는 중…