Water → HCID 69735448, compound

HRID 379568Notes

Reaction equation

HRID 379568 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:15]1[CH:16]=[CH:17][C:18]2[O:22][C:21]([S:23](Cl)(=[O:25])=[O:24])=[CH:20][C:19]=2[CH:27]=1.O.[Cl:29]CCl>C(OCC)C>[Cl:29][CH:2]1[CH2:3][N:4]([S:23]([C:21]2[O:22][C:18]3[CH:17]=[CH:16][CH:15]=[CH:27][C:19]=3[CH:20]=2)(=[O:24])=[O:25])[CH2:5][CH2:6][NH:1]1

Participants

7

Reactant 5

HCID 962WaterHCID 4837PiperazineHCID 6344Dichloromethane2×HCID 8471TriethylamineHCID 151586095-Chlorobenzofuran-2-sulfonyl Chloride

Product 1

HCID 69735448HCID 69735448, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A stirred solution of piperazine (1.15 g, 13.4 mmol) and triethylamine (4.7 ml, 46.5 mmol) in dichloromethane (30 ml) was cooled to −5° C., and a solution of 5-chlorobenzofuran-2-sulphonyl chloride (1.69 g, 7.8 mmol) in dichloromethane (10 ml) was added. Stirring was continued for 15 mins, and the reaction mixture then allowed to warm to ambient temperature over 2 hrs with stirring. Water was added to the reaction mixture, and the organic layer separated; this was washed with water (twice), brine (once), then dried (MgSO4), filtered and evaporated to give a yellow gum. This was chromatographed (Merck Art 9385 silica, eluting with dichloromethane containing increasing amounts of methanol, up to 10% v/v) to give a yellow solid; trituration with diethyl ether gave 5-chlorobenzofuran-2-ylsulphonyl piperazine as a colourless solid (1.11 g) which was used without further purification, 1H NMR (CDCl3) δ=2.8-3.0 ppm (t, 4H), δ=3.2-3.4 ppm (t, 4H), δ=7.3 ppm (s, 1H), δ=7.45 ppm (dd, 2H), δ=7.7 ppm (s, 1H); MS (M+H)+ 301/303.

Workup

  1. stirringwith stirring
  2. customthe organic layer separated
  3. washthis was washed with water (twice), brine (once),
  4. dry with materialthen dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give a yellow gum
  8. customThis was chromatographed (Merck Art 9385 silica
  9. washeluting with dichloromethane containing
  10. temperatureincreasing amounts of methanol
  11. customup to 10% v/v) to give a yellow solid

Sources & evidence

ORD record
ord-a16c893bb4ed4de9a5bfd60d9588a7ac
Source dataset
uspto-grants-2001_10
Patent number
US06300330B1

Reaction notes

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