Triethylamine → 1-(4-Bromophenyl)-4-(methylsulfonyl)piperazine

HRID 1244435Notes

Reaction equation

HRID 1244435 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>ClCCl>[Br:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][N:12]([S:23]([CH3:22])(=[O:25])=[O:24])[CH2:11][CH2:10]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 144228381-(4-Bromophenyl)piperazine hydrochloride

Product 1

HCID 219193841-(4-Bromophenyl)-4-(methylsulfonyl)piperazineYield 81.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(4-bromophenyl)piperazine hydrochloride (5.09 g, 18.3 mmol) and triethylamine (7.67 ml) in dichloromethane (100 ml) was added methanesulfonyl chloride (2.83 ml, 36.3 mmol) dropwise. The mixture was stirred for 1 hour at room temperature then dichloromethane (100 ml) was added. The organics were washed with water (2×), brine and dried (Na2SO4) and evaporated in vacuo to a yellow solid which crystallised from Ethanol and washed with diethyl ether to give 1-(4-bromophenyl)-4-(methanesulfonyl)piperazine (4.74 g, 81% yield) as a white fluffy powder.

Workup

  1. washThe organics were washed with water (2×), brine
  2. dry with materialdried (Na2SO4)
  3. customevaporated in vacuo to a yellow solid which
  4. customcrystallised from Ethanol
  5. washwashed with diethyl ether

Sources & evidence

ORD record
ord-392ea25d85eb4afea7bc91170b4028bd
Source dataset
uspto-grants-2006_10
Patent number
US07122551B2

Reaction notes

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