Piperazine → 1-((4-Methoxyphenyl)sulfonyl)piperazine

HRID 908273Notes

Reaction equation

HRID 908273 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[NH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.[K+].[Br-]>C(Cl)Cl.N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 4837Piperazine3×HCID 74014-Methoxybenzenesulfonyl chlorideHCID 253877Potassium Bromide

Product 1

HCID 7975601-((4-Methoxyphenyl)sulfonyl)piperazineYield 88%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-methoxybenzenesulfonyl chloride (6.2 g, 30 mM) in CH2Cl2 (180 ml) is added to a solution of piperazine (12.9 g, 150 mM) in CH2Cl2 (570 ml) and pyridine (2.7 ml). The solution is maintained in agitation at room temperature for 15 h. The solvent is then removed under vacuum. The residue is dissolved in 3N HCl and washed with ethyl ether. The organic phase is removed and the aqueous phase is alkalized and extracted with ethyl acetate. The organic phase is dried over Na2SO4 and the solvent is removed under vacuum. A white solid is obtained (Yield=88%). P.f.: 184.3-185.6° C. FT-IR (KBr): 3082, 3058, 2975, 2944, 2907, 2840, 2810, 1597, 1580, 1495, 1465, 1442, 1413, 1346, 1318, 1298, 1286, 1254, 1179, 1159, 1110, 1095, 1066, 1027, 947, 830, 805, 734, 657, 634 cm−1. 1NMRs (300 MHz CDCl3, δ): 2.48-2.51 (m, 4H, two CH2 piperazine), 2.88-2.94 (m, 5H, two CH2 piperazine and NH), 3.86 (s, 3H, OCH3), 6.95-7.00 (m, 2H, aromatic protons), 7.64-7.68 (m, 2H, aromatic protons). 13C NMRs (75 MHz CDCl3, δ): 46.25, 50.57, 55.85, 77.82, 77.25, 77.67, 79.95, 114.40, 114.58, 127.32, 130.12, 163.27. GC-MS (70 eV) m/z (int. rel.): 258 [(34S)M+, 1], 256 [(32S)M+, 10], 171 (8), 108 (7), 92 (10), 85 (100), 77 (11), 64 (6), 63 (4), 56 (30). Anal. (C11H16N2O3S): Cal.: C, 51.54; H, 6.29; N, 10.93. Found: C, 51.59; H, 6.25; N, 10.96.

Workup

  1. customThe solvent is then removed under vacuum
  2. dissolutionThe residue is dissolved in 3N HCl
  3. washwashed with ethyl ether
  4. customThe organic phase is removed
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic phase is dried over Na2SO4
  7. customthe solvent is removed under vacuum
  8. customA white solid is obtained (Yield=88%)
  9. custom184.3-185.6° C

Sources & evidence

ORD record
ord-83cd0ae94d4044dba96c261947346e59
Source dataset
uspto-grants-2011_09
Patent number
US08017613B2

Reaction notes

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