Benzenesulfonyl chloride → 1-[2-(2,4-Difluorophenyl)ethyl]-4-phenylsulphonylpiperazine

HRID 23328Notes

Reaction equation

HRID 23328 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+]>CC#N>[F:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[CH2:19][CH2:20][N:21]1[CH2:22][CH2:23][N:24]([S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[CH2:25][CH2:26]1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 225738841-[2-(2,4-Difluorophenyl)ethyl]piperazine

Product 1

HCID 97992831-[2-(2,4-Difluorophenyl)ethyl]-4-phenylsulphonylpiperazineYield 23%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Benzene sulphonyl chloride (0.15 g), the foregoing amine (0.193 g) and potassium carbonate (0.118 g) were heated together in MeCN (10 ml). Reaction was monitored by mass spectroscopy, and was completed after 2 h. The reaction mixture was cooled to room temperature, quenched with water and extracted into ethyl acetate. The organic extracts were combined, washed with water, dried (MgSO4) and concentrated to give a dark orange solid. This solid was purified by dry flash chromatography using SiO2, CH2Cl2 to 5% MeOH:CH2Cl2, followed by recrystallisation using pet. ether and CH2Cl2 to give the title product as a pale yellow solid (23%). MS: (M+H)+=367. δH (360 MHz, CDCl3): 2.50-2.60 (6H, m), 2.66-2.74 (2H, m), 3.02-3.10 (4H, m), 6.70-6.80 (2H, m), 7.05-7.14 (1H, m), 7.50-7.56 (2H, m), 7.56-7.62 (1H, m), 7.74-7.80 (2H, m). CHN C18H20 F2N2O2S: calc. C=59.00, H=5.50, N=7.65%; found C=59.12, H=5.43, N=7.56%.

Workup

  1. customReaction
  2. customquenched with water
  3. extractionextracted into ethyl acetate
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customto give a dark orange solid
  8. customThis solid was purified
  9. customby dry flash chromatography
  10. customCH2Cl2, followed by recrystallisation

Sources & evidence

ORD record
ord-a434e492f78c49ce84d1dc1153f24929
Source dataset
uspto-grants-2005_02
Patent number
US06852718B2

Reaction notes

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