Water → HCID 20186508, compound

HRID 2309026Notes

Reaction equation

HRID 2309026 reaction equation
[ClH:1].Cl.[Cl:3][C:4]1[CH:20]=[CH:19][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][SH:18])[CH2:11][CH2:10]2)=[CH:6][CH:5]=1.[OH-].[Na+].O.[Cl:24][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][N:30]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=2)[CH2:29][CH2:28]1>C(O)C>[ClH:3].[ClH:24].[ClH:1].[ClH:3].[Cl:40][C:37]1[CH:38]=[CH:39][C:34]([CH2:33][N:30]2[CH2:31][CH2:32][N:27]([CH2:26][CH2:25][S:18][CH2:17][CH2:16][CH2:15][N:12]3[CH2:11][CH2:10][N:9]([CH2:8][C:7]4[CH:19]=[CH:20][C:4]([Cl:3])=[CH:5][CH:6]=4)[CH2:14][CH2:13]3)[CH2:28][CH2:29]2)=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 12362126HCID 12362126, compoundHCID 137311183-[4-(4-Chlorobenzyl)piperazin-1-yl]propanethiol dihydrochloride

Product 1

HCID 20186508HCID 20186508, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 3-[4-(4-chlorobenzyl)piperazine-1-yl]propanethiol dihydrochloride (2 g), sodium hydroxide (0.3 g), water (10 ml), and ethanol (100 ml) is refluxed for 15 minutes, and then a solution of 1-(2-chloroethyl)-4-(4-chlorobenzyl)piperazine (1.9 g) in ethanol (20 ml) is added. The resulting mixture is refluxed for 2 hours and the ethanol is removed in vacuo. Water is added to the residue and the product is extracted with methylene chloride, dried (magnesium sulfate), and concentrated. The resulting oil is purified on a silica gel column (methylene chloride: methanol, 9:1), and then dissolved in ether. The product is precipitated with ethereal hydrochloric acid and recrystallized from aqueous ethanol to provide 1.2 g of {2-[4-(4-chlorobenzyl)piperazin-1-yl)ethyl}{3-[4-(4-chlorobenzyl)piperazin-1-yl]propyl}sulfide tetrahydrochloride as colorless crystals, m.p. 292°-295° C.

Workup

  1. temperatureis refluxed for 15 minutes
  2. temperatureThe resulting mixture is refluxed for 2 hours
  3. customthe ethanol is removed in vacuo
  4. additionWater is added to the residue
  5. extractionthe product is extracted with methylene chloride
  6. dry with materialdried (magnesium sulfate)
  7. concentrationconcentrated
  8. customThe resulting oil is purified on a silica gel column (methylene chloride: methanol, 9:1)
  9. dissolutiondissolved in ether
  10. customThe product is precipitated with ethereal hydrochloric acid
  11. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-82ae0bb0ac5549b18556205a9a7e9949
Source dataset
uspto-grants-1987_09
Patent number
US04692448

Reaction notes

Loading…