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

HRID 557776

反応式

HRID 557776 の反応式
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]

参加物

5

反応物 3

HCID 9590p-FluoronitrobenzeneHCID 81531DiisopropylethylamineHCID 424914Methyl isonipecotate

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
150 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a53dc576db814d0182597ed153ed5dee
出典データセット
uspto-grants-2011_11
特許番号
US08058299B2

関連ノート

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