Piperidine → 2-Nitro-5-piperidinoaniline

HRID 884411ノート

反応式

HRID 884411 の反応式
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=1.[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N+:9]([C:5]1[CH:4]=[CH:3][C:2]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:7][C:6]=1[NH2:8])([O-:11])=[O:10]

参加物

5

反応物 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 742185-Chloro-2-nitroaniline

生成物 1

HCID 70622462-Nitro-5-piperidinoaniline収率 22%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

A mixture of 5-chloro-2-nitrophenylamine (5 g, 29 mmol), piperidine (2.9 mL, 29 mmol), and K2CO3 (4.0 g, 29 mmol) in DMF (20 mL) was stirred at 120° C. for 4 h. The reaction mixture was cooled to room temperature and poured into ice cold water (100 mL). The crude solid product was collected by filtration, air dried, and purified by flash chromatography (silica gel, 4×15 cm, eluted with CHCl3) to yield the product as orange crystals (1.4 g, 22%). See, Aust. J. Chem., 47:247-262 (1994).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe crude solid product was collected by filtration, air
  3. customdried
  4. custompurified by flash chromatography (silica gel, 4×15 cm, eluted with CHCl3)

出典と根拠

ORDレコード
ord-0aa8436d97014a5fb97cbd5a648594e7
出典データセット
uspto-grants-2012_08
特許番号
US08242115B2

反応ノート

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