p-Bromobenzenesulfonyl chloride → 4-Bromo-N-(1-ethyl-3-piperidinyl)benzenesulfonamide

HRID 736608Notes

Reaction equation

HRID 736608 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([CH2:8][CH3:9])[CH2:3]1.[Br:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1>C(Cl)Cl>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([NH:1][CH:2]2[CH2:7][CH2:6][CH2:5][N:4]([CH2:8][CH3:9])[CH2:3]2)(=[O:19])=[O:18])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 980943-amino-N-ethylpiperidine

Product 1

HCID 103377214-Bromo-N-(1-ethyl-3-piperidinyl)benzenesulfonamideYield 98.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Amino-1-ethylpiperidine (0.4 mL, 3.13 mmol) was added to a solution of 4-bromo-benzenesulfonyl chloride (0.4 g, 1.56 mmol) in methylene chloride (10 mL) at room temperature. The mixture was stirred overnight. The reaction solution was extracted three times with a aqueous saturated sodium hydrogen carbonate solution, dried (MgSO4) and evaporated to give 0.533 g (93% yield) of the title compound as a light brown solid: 1H NMR (CDCl3) δ 7.74 (d, J=9 Hz, 2H), 7.62 (d, J=9 Hz, 2H), 3.45 (br s, 1H), 2.46 (br s, 1H), 2.27 (m, 2H), 2.23 (m, 2H), 2.13 (m, 1H), 1.64 (m, 1H), 1.45 (m, 3H), 0.93 (t, J=7 Hz, 3H); 13C NMR (CDCl3) δ 140.7, 132.5, 128.7, 127.5, 53.2, 52.3, 49.7, 21.9, 12.1; MS (ESP) m/z 347, 349 (M++1).

Workup

  1. extractionThe reaction solution was extracted three times with a aqueous saturated sodium hydrogen carbonate solution
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-728bdfdfae744730b8d232374b9683bb
Source dataset
uspto-grants-2009_09
Patent number
US07595319B2

Reaction notes

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