Thiazolidinedione → 5-[4-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-benzylidene]-thiazolidine-2,4-dione

HRID 1061218Notes

Reaction equation

HRID 1061218 reaction equation
C(=O)C1C=CC=CC=1.[O:9]1[C:13]2([CH2:18][CH2:17][N:16]([C:19]3[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)[O:12][CH2:11][CH2:10]1.[S:27]1[CH2:31][C:30](=[O:32])[NH:29][C:28]1=[O:33].N1CCCCC1>C(O)C>[O:9]1[C:13]2([CH2:18][CH2:17][N:16]([C:19]3[CH:26]=[CH:25][C:22]([CH:23]=[C:31]4[S:27][C:28](=[O:33])[NH:29][C:30]4=[O:32])=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)[O:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 222204854-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-benzaldehyde benzaldehyde

Product 1

HCID 731781995-[4-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-benzylidene]-thiazolidine-2,4-dioneYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-benzaldehyde benzaldehyde (Taylor, E. C., Skotnicki, J. S. Synthesis, 1981, 606) (15 g, 60 mol), 2,4-thiazolidinedione (7.0 g, 60 mmol), and piperidine (8.0 mL, 81.2 mmol) in 450 mL of ethanol was refluxed for 6 hours. The solid which was formed on cooling the solution was collected to give the title compound as an orange solid (20.5 g, 99%); 1H NMR (300 MHz, DMSO-d6) δ 1.67 (t, J=5.6 Hz, 4H), 3.47 (t, J=5.6 Hz, 4H), 3.92 (s, 4H), 7.07 (d, J=9.0 Hz, 2H), 7.43 (d, J=9.0 Hz, 2H), 7.67 (s, 1H), 12.40 (brs, 1H); MS (ES) m/z: 346.8 (MH+); HRMS Calcd. for C17H19N2O4S(MH+): 346.0987. Found: 346.0994. Anal. Calcd. for C17H18N2O4S: C, 58.94; H, 5.24; N, 8.09. Found: C, 58.92; H, 5.11; N, 7.96.

Workup

  1. temperaturewas refluxed for 6 hours
  2. customThe solid which was formed
  3. temperatureon cooling the solution
  4. customwas collected

Sources & evidence

ORD record
ord-640107c9b8ff43f98111fe94973dc804
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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