Pyridine → tert-Butyl 4-{2-[(methylsulfonyl)amino]phenyl}piperidinecarboxylate

HRID 489644노트

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HRID 489644 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1.N1C=CC=CC=1.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>ClCCCl>[CH3:27][S:28]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13]1)(=[O:30])=[O:29]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 22266191tert-Butyl 4-(2-aminophenyl)piperidine-1-carboxylate

생성물 1

HCID 22266209tert-Butyl 4-{2-[(methylsulfonyl)amino]phenyl}piperidinecarboxylate수율 82.3%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

반응 조건

온도
25 °C

실험 절차

To a 100 mL round-bottomed flask was added tert-butyl 4-(2-aminophenyl)piperidinecarboxylate (Preparation B) (1.93 g, 7.2 mmol) and 1,2-dichloroethane (50 mL). The solution was magnetically stirred under a N2 atmosphere, treated with pyridine (2.9 mL, 36 mmol) and methanesulfonyl chloride (Aldrich) (1.1 mL, 1.7 g, 14 mmol). The vessel was immersed in a 50° C. oil bath for 6 h then cooled to 25° C. The solvent was removed in vacuo, and the residue was partitioned between EtOAc (200 mL) and 1 N HCl (100 mL). The organic layer was washed with satd NaHCO3 (75 mL), satd NaCl (50 mL), dried over Na2SO4, filtered and concentrated to give a foam. The foam was purified by silica gel chromatography (3:/EtOAc:hexane) to provide the title compound as a white foam (2.1 g). MS (ESI, pos. ion) m/z: 355 (M+1); (ESI, neg. ion) m/z: 353 (M−1). Calc'd for C17H26N2O4S: 354.47.

후처리

  1. customwas immersed in a 50° C.
  2. customfor 6 h
  3. customThe solvent was removed in vacuo
  4. customthe residue was partitioned between EtOAc (200 mL) and 1 N HCl (100 mL)
  5. washThe organic layer was washed with satd NaHCO3 (75 mL), satd NaCl (50 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a foam
  10. customThe foam was purified by silica gel chromatography (3:/EtOAc:hexane)

출처 및 근거

ORD 기록
ord-63ecb60233a941ce84226f6a9cc5f46f
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06977264B2

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