p-Fluoronitrobenzene → Methyl 1-(4-nitrophenyl)piperidine-4-carboxylate

HRID 1641854

반응식

HRID 1641854 반응식
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][O:12][C:13]([CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)=[O:14].C(N(C(C)C)CC)(C)C>C1COCC1>[CH3:11][O:12][C:13]([CH:15]1[CH2:20][CH2:19][N:18]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:17][CH2:16]1)=[O:14]

참가 물질

5

반응물 3

HCID 9590p-FluoronitrobenzeneHCID 81531DiisopropylethylamineHCID 424914Methyl isonipecotate

생성물 1

HCID 345002Methyl 1-(4-nitrophenyl)piperidine-4-carboxylate수율 37.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
150 °C

실험 절차

To a solution of 4-fluoronitrobenzene (0.70 g, 4.96 mmol) in THF (8 mL) was added piperadine-4-carboxylic acid methyl ester (0.71 g, 4.96 mmol) and diisopropylethylamine (0.66 g, 5.11 mmol). The mixture was heated in a microwave oven at 150° C. for 1.5 hr. The resulting mixture was extracted with ethyl acetate and hydrochloric acid (0.2 N). The organic layer was washed with brine and concentrated sodium bicarbonate solution. After the evaporation of solvents, the residue was purified through a Biotage flash column chromatography using ethyl acetate and hexanes (1:1 ratio) to give a yellow solid as 1-(4-nitrophenyl)-piperidine-4-carboxylic acid methyl ester (490 mg). 1H-NMR is consistent with the structure.

후처리

  1. extractionThe resulting mixture was extracted with ethyl acetate and hydrochloric acid (0.2 N)
  2. washThe organic layer was washed with brine and concentrated sodium bicarbonate solution
  3. customAfter the evaporation of solvents
  4. customthe residue was purified through a Biotage flash column chromatography

출처 및 근거

ORD 기록
ord-e70ec3731a904dd5af0c318acc04c0d5
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08115011B2

연결된 노트

불러오는 중…