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

HRID 859922Notes

Reaction equation

HRID 859922 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]>C(Cl)Cl>[CH3:22][S:23]([N:12]1[CH2:13][CH2:14][N:9]([C:6]2[CH:5]=[CH:4][C:3]([Br:2])=[CH:8][CH:7]=2)[CH2:10][CH2:11]1)(=[O:25])=[O:24]

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, CAS number 68104-62-1) and triethylamine (7.67 mL), in CH2Cl2 was added methanesulfonyl chloride (2.83 mL, 36.3 mmol) dropwise. The mixture was stirred for one hour at RT, then CH2Cl2 (100 mL) was added. The organics were washed with water (2×100 mL), and evaporated in vacuo to give a yellow solid which crystallised from ethanol and was washed with ether to give 1-(methylsulfonyl)-4-(4-bromophenyl)piperazine as a white powder (4.74 g, 81%).

Workup

  1. washThe organics were washed with water (2×100 mL)
  2. customevaporated in vacuo
  3. customto give a yellow solid which
  4. customcrystallised from ethanol
  5. washwas washed with ether

Sources & evidence

ORD record
ord-aad918fc574f46dd9b8581532cb3cf38
Source dataset
uspto-grants-2006_12
Patent number
US07153857B2

Reaction notes

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