Acetone → N-Benzyl-N-(3,4-dimethoxy-phenyl)-4-(4-oxo-piperidin-1-yl)-benzenesulfonamide

HRID 1278737Notes

Reaction equation

HRID 1278737 reaction equation
[CH2:1]([N:8]([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([O:36][CH3:37])[CH:29]=1)[S:9]([C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:27][CH2:26][C:21]3(OCC[O:22]3)[CH2:20][CH2:19]2)=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=O>Cl>[CH2:1]([N:8]([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([O:36][CH3:37])[CH:29]=1)[S:9]([C:12]1[CH:13]=[CH:14][C:15]([N:18]2[CH2:27][CH2:26][C:21](=[O:22])[CH2:20][CH2:19]2)=[CH:16][CH:17]=1)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 180AcetoneHCID 12051786N-Benzyl-N-(3,4-dimethoxy-phenyl)-4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-benzenesulfonamide

Product 1

HCID 11488488N-Benzyl-N-(3,4-dimethoxy-phenyl)-4-(4-oxo-piperidin-1-yl)-benzenesulfonamideYield 709.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

N-Benzyl-N-(3,4-dimethoxy-phenyl)-4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-benzenesulfonamide(0.10 g, 0.19 mM) was stirred in 6M HCl (2 ml) and acetone(5 ml) at 60° C. overnight. The reaction mixture was basified with 5N NaOHaq. (until pH>7) and washed with ethyl acetate (3×10 ml). The organic extracts were dried with sodium sulfate, passed through a plug of magnesol, concentrated and triturated with hexanes to afford 0.65 g of the desired product as a white solid. H1 NMR(CDCl3) δ 2.58(t, 4H, J=6.06 Hz), 3.67(s, 3H), 3.74(t, 4H, J=6.12 Hz), 3.81(s, 3H), 4.71(s, 2H), 6.48(m, 3H), 6.67(d, 1H, J=8.46 Hz), 6.93(d, 2H), J=9.9 Hz), 7.20(m, 4H), 7.59(d, 2H, J=4.71 Hz). MS(ES) m/z 481.0; (MH+); HRMS for C26H28SN2O5: 481.1778.

Workup

  1. customat 60° C.
  2. customovernight
  3. wash(until pH>7) and washed with ethyl acetate (3×10 ml)
  4. dry with materialThe organic extracts were dried with sodium sulfate
  5. concentrationconcentrated
  6. customtriturated with hexanes

Sources & evidence

ORD record
ord-74842254e8eb4795b51a430ee599c609
Source dataset
uspto-grants-2002_09
Patent number
US06444685B1

Reaction notes

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