3-Aminobenzonitrile → 1-(3-Cyanophenyl)piperazine

HRID 276894

反応式

HRID 276894 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].Cl.Cl[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]Cl>C1(C)C(C)=CC=CC=1.[OH-].[Na+]>[C:5]([C:4]1[CH:3]=[C:2]([N:1]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH:9]=[CH:8][CH:7]=1)#[N:6]

参加物

5

反応物 2

HCID 167023-AminobenzonitrileHCID 522769Bis(2-chloroethyl)amine hydrochloride

生成物 1

HCID 114809021-(3-Cyanophenyl)piperazine収率 34%

試薬・触媒・溶媒 2

HCID 7237O-Xylene溶媒HCID 14798Sodium Hydroxide溶媒

反応条件

温度
155 °C

実験手順

3-Aminobenzonitrile (6.1 g, 52 mmol) and bis(2-chloroethyl)amine hydrochloride (10 g, 57 mmol) were dissolved in xylene (100 ml), and the resulting solution was stirred at 150 to 160° C. for 5 hours. Supernatant fluid of the reaction solution was discarded, the remaining residue was dissolved in sodium hydroxide aqueous solution (1 N) and then the reaction product was extracted therefrom with ethyl acetate. The extract was washed with saturated brine, and then the compound obtained by the evaporation of the solvent under a reduced pressure was separated and purified by a silica gel column chromatography to obtain 3.2 g of the title compound (17 mmol, 34% in yield). A portion of the thus obtained compound was made into hydrochloric acid salt by treating it with hydrochloric acid-saturated methanol.

後処理

  1. extractionthe reaction product was extracted
  2. washThe extract was washed with saturated brine
  3. customthe compound obtained by the evaporation of the solvent under a reduced pressure
  4. customwas separated
  5. custompurified by a silica gel column chromatography

出典と根拠

ORDレコード
ord-16226fadb74f4ca2baebda3f682e8192
出典データセット
uspto-grants-2002_03
特許番号
US06355642B1

関連ノート

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