4-Toluenesulfonyl chloride → 3-(4-Methyl-piperazin-1-yl)propyl-4-toluene sulphonate

HRID 723496Notes

Reaction equation

HRID 723496 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[OH:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]1.C(N(CC)CC)C>C(Cl)Cl>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:12][CH2:13][CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][N:19]([CH3:22])[CH2:20][CH2:21]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 792083-(4-Methyl-1-piperazine)propan-1-ol

Product 1

HCID 218748183-(4-Methyl-piperazin-1-yl)propyl-4-toluene sulphonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Toluenesulphonyl chloride (3.2 g) was added to a stirred mixture of 1-(3-hydroxypropyl)-4-methylpiperazine (2.4 g), triethylamine (4.6 ml) and methylene chloride (60 ml) and the resultant mixture was stirred at ambient temperature for 2 hours. The solution was washed in turn with a saturated aqueous sodium bicarbonate solution and with water and filtered through phase separating paper. The organic filtrate was evaporated to give 3-(4-methylpiperazin-1-yl)propyl 4-toluenesulphonate as an oil which crystallised on standing (3.7 g); Mass Spectrum: M+H+ 313.

Workup

  1. washThe solution was washed in turn with a saturated aqueous sodium bicarbonate solution and with water
  2. filtrationfiltered through phase
  3. customseparating paper
  4. customThe organic filtrate was evaporated

Sources & evidence

ORD record
ord-2273ac38d25a407cb896eeb69c8b5008
Source dataset
uspto-grants-2006_11
Patent number
US07141577B2

Reaction notes

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