Potassium Hydroxide → 1,1'-(Dithiodi-2,1-ethanediyl)bis[4-(4-cyanobenzyl)piperazine]

HRID 2309027ノート

反応式

HRID 2309027 の反応式
[C:1]([C:3]1[CH:15]=[CH:14][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:5][CH:4]=1)#[N:2].Cl[CH2:17][CH2:18][S:19][S:20][CH2:21][CH2:22]Cl.[OH-].[K+]>CS(C)=O>[CH2:17]([N:11]1[CH2:12][CH2:13][N:8]([CH2:7][C:6]2[CH:14]=[CH:15][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH2:9][CH2:10]1)[CH2:18][S:19][S:20][CH2:21][CH2:22][N:11]1[CH2:12][CH2:13][N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:15][CH:14]=2)[CH2:9][CH2:10]1

参加物

5

反応物 3

HCID 14797Potassium HydroxideHCID 94964Disulfide, bis(2-chloroethyl)HCID 20608924-[(Piperazin-1-yl)methyl]benzonitrile

生成物 1

HCID 139148641,1'-(Dithiodi-2,1-ethanediyl)bis[4-(4-cyanobenzyl)piperazine]収率 85%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
80 °C

実験手順

A mixture of 4-cyanobenzylpiperazine (4.0 g), bis(2-chloroethyl) disulfide (1.9 g), potassium hydroxide (5.0 g), and dimethylsulfoxide (50 ml) is heated at 80° C. until the solution turns pink in color. The heat is then removed and the reaction mixture allowed to stir overnight at room temperature. The solution is diluted with water, and the product extracted with ether, dried, and concentrated to give 4.4 g of an oil, which is purified on a silica gel column (methylene chloride: methanol, 98:2). The resulting light brown oil is dissolved in ether and the salt precipitated with ethereal hydrochloric acid to give, after recrystallization from aqueous ethanol, 1,1'-(dithiodi-2,1-ethanediyl)bis[4-(4-cyanobenzyl)piperazine] tetrahydrochloride as a white crystalline solid, m.p. 272°-275° C.

後処理

  1. customThe heat is then removed
  2. additionThe solution is diluted with water
  3. extractionthe product extracted with ether
  4. customdried
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-1a3335a8e3b448bfa95584de6fb15978
出典データセット
uspto-grants-1987_09
特許番号
US04692448

反応ノート

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