1-Benzylpiperazine → HCID 26945817, compound

HRID 748513Notes

Reaction equation

HRID 748513 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:14][C:15]1[N:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>C(Cl)Cl>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([S:21]([C:18]2[CH:19]=[N:20][C:15]([Cl:14])=[CH:16][CH:17]=2)(=[O:23])=[O:22])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 759941-BenzylpiperazineHCID 27927922-Chloro-5-pyridinesulfonyl chloride

Product 1

HCID 26945817HCID 26945817, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of benzylpiperazine (0.45 mL, 2.59 mmol) in methylene chloride (15 mL), cooled on an ice-bath, was 6-chloropyridine-3-sulfonyl chloride (0.50 g, 2.36 mmol; described in: Naegeli, C. et al. Helv. Chim. Actal. 1938, 21, 1746-1750) dissolved in methylene chloride (10 mL) added slowly. The reaction was stirred for 30 min and the formed white precipitation was filtered and washed with methylene chloride and water affording, after drying, 0.68 g (82% yield) of the title compound: 1H NMR (DMSO-d6, 400 MHz) δ 8.70 (d, J=3 Hz, 1 H), 8.14 (dd, J=8, 3 Hz, 1 H), 7.76 (d, J=8 Hz, 1 H), 7.50-7.43 (m, 2 H), 7.38-7.30 (m, 3 H), 4.23 (br s, 2 H), 3.79-3.63 (m, 2 H), 3.45-3.18 (m, 2 H), 3.11-2.96 (m, 2 H), 2.96-2.81 (m, 2 H); MS (ES) m/z 352 (M++1).

Workup

  1. additionadded slowly
  2. customthe formed white precipitation
  3. filtrationwas filtered
  4. washwashed with methylene chloride and water affording
  5. customafter drying

Sources & evidence

ORD record
ord-dc4c0e7bab0b40f7911ebf85d1fcc03f
Source dataset
uspto-grants-2008_07
Patent number
US07399780B2

Reaction notes

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