Piperidine → 3-Nitro-4-piperidin-1-ylpyridine

HRID 69827

반응식

HRID 69827 반응식
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>C(O)C>[N+:8]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:2]=1[N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)([O-:10])=[O:9]

참가 물질

4

반응물 2

HCID 8082PiperidineHCID 27357814-Chloro-3-nitropyridine

생성물 1

HCID 35076693-Nitro-4-piperidin-1-ylpyridine수율 95%

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

A solution of 4-chloro-3-nitropyridine (1.0 equiv.) and piperidine (2.0 equiv.) in ethanol, at a concentration of 0.5 M, was stirred at rt for 48 hours at which time the ethanol was removed in vacuo. The residue was partitioned between EtOAc (300 mL) and Na2CO3(sat) (75 mL), was washed further with H2O (50 mL), NaCl(sat.) (50 mL), was dried over MgSO4, was filtered and the volatiles were removed in vacuo yielding 3-nitro-4-(piperidin-1-yl)pyridine (95%). LCMS (m/z): 207.7 (MH+); LC Rt=1.60 min. 1H NMR (CDCl3): δ 8.80 (s, 1H), 8.31 (d, J=5.7, 1H), 6.84 (d, J=6.3, 1H), 3.18-3.21 (m, 4H), 1.64-1.78 (m, 6H).

후처리

  1. customwas removed in vacuo
  2. customThe residue was partitioned between EtOAc (300 mL) and Na2CO3(sat) (75 mL)
  3. washwas washed further with H2O (50 mL), NaCl(sat.) (50 mL)
  4. dry with materialwas dried over MgSO4
  5. filtrationwas filtered
  6. customthe volatiles were removed in vacuo

출처 및 근거

ORD 기록
ord-abee4ba2c18f413e9380fa98234b3b93
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822497B2

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