Dimethyl Sulfoxide → 1-(4-Methylbenzyl)-4-(3-chloropropyl)piperazine dihydrochloride

HRID 2290864

反応式

HRID 2290864 の反応式
[CH3:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[OH-].[K+].CS(C)=O.Br[CH2:22][CH2:23][CH2:24][Cl:25]>O>[ClH:25].[ClH:25].[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]([CH2:22][CH2:23][CH2:24][Cl:25])[CH2:9][CH2:8]2)=[CH:13][CH:14]=1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 80061-Bromo-3-chloropropaneHCID 14797Potassium HydroxideHCID 7647231-(4-Methylbenzyl)piperazine

生成物 1

HCID 201531921-(4-Methylbenzyl)-4-(3-chloropropyl)piperazine dihydrochloride収率 274.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 14.0 g of 1-(4-methylbenzyl)piperazine, 8.0 g of potassium hydroxide and 125 ml of dimethyl sulfoxide was stirred for 45 minutes. 11.8 g of 1-bromo-3-chloropropane were then added, and the mixture was stirred for an additional hour. Water was added, and the product was extracted with ether, and the extract was dried (sodium sulfate) and treated with ethereal hydrochloric acid to give 23.3 g (94% of theory) of 1-(4-methylbenzyl)-4-(3-chloropropyl)piperazine dihydrochloride as a white crystalline solid. (b) The procedure described in Example 1(b) was followed, using 7.7 g of thiourea, 23.0 g of 1-(4-methylbenzyl)-4-(3-chloropropyl)piperazine dihydrochloride, 6.5 g of triethylamine and 250 ml of reagent ethanol. The hydrolysis was effected with 6.0 g of sodium hydroxide in 40 ml of water. Work-up, as described above, gave 16.4 g (72% of theory) of 3-[4-(4-methylbenzyl)piperazin-1-yl] propanethiol dihydrochloride as a white crystalline solid, M.p. 273°-277° C. (dec.).

後処理

  1. stirringthe mixture was stirred for an additional hour
  2. extractionthe product was extracted with ether
  3. dry with materialthe extract was dried (sodium sulfate)
  4. additiontreated with ethereal hydrochloric acid

出典と根拠

ORDレコード
ord-a09eccbe7ed047dd8ec4889ccede0e3a
出典データセット
uspto-grants-1986_10
特許番号
US04618677

関連ノート

読み込み中…