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

HRID 454161Notes

Reaction equation

HRID 454161 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH3:11])[CH2:7][CH2:6]1.C(N(CC)CC)C.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>ClCCl>[CH3:11][N:8]1[CH2:7][CH2:6][N:5]([CH2:4][CH2:3][CH2:2][O:1][S:25]([C:22]2[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=2)(=[O:27])=[O:26])[CH2:10][CH2:9]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

A solution of 1-(3-hydroxypropyl)-4-methylpiperazine (2.4 g, 15 mmol), (prepared as described for the starting material in Example 133), in dichloromethane (60 ml) was treated with triethylamine (4.6 ml, 33 mmol) and p-toluenesulphonyl chloride (3.2 g, 17 mmol) and stirred at ambient temperature for 2 hours. The solution was washed with saturated aqueous sodium hydrogen carbonate solution followed by water and filtered through phase separating paper. The filtrate was evaporated under vacuum to give 3-(4-methyl-piperazin-1-yl)propyl-4-toluene sulphonate as an oil which crystallised on standing (3.7 g, 78%).

Workup

  1. washThe solution was washed with saturated aqueous sodium hydrogen carbonate solution
  2. filtrationfiltered through phase
  3. customseparating paper
  4. customThe filtrate was evaporated under vacuum

Sources & evidence

ORD record
ord-71c4225be880496d85b6b3d464141278
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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