Piperidine → 5-[4-(2,2-Diethoxy-ethoxy)-benzylidene]-2-piperidin-1-yl-thiazol-4-one

HRID 2188278Notes

Reaction equation

HRID 2188278 reaction equation
[CH2:1]([O:3][CH:4]([O:21][CH2:22][CH3:23])[CH2:5][O:6][C:7]1[CH:20]=[CH:19][C:10]([CH:11]=[C:12]2[S:16][C:15](=S)[NH:14][C:13]2=[O:18])=[CH:9][CH:8]=1)[CH3:2].S1CC(=O)NC1=S.[NH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>C(O)C>[CH2:1]([O:3][CH:4]([O:21][CH2:22][CH3:23])[CH2:5][O:6][C:7]1[CH:20]=[CH:19][C:10]([CH:11]=[C:12]2[S:16][C:15]([N:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)=[N:14][C:13]2=[O:18])=[CH:9][CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 1201546RhodanineHCID 739906085-[4-(2,2-Diethoxy-ethoxy)-benzylidene]-2-thioxo-thiazolidin-4-one2×

Product 1

HCID 699228865-[4-(2,2-Diethoxy-ethoxy)-benzylidene]-2-piperidin-1-yl-thiazol-4-oneYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-[4-(2,2-diethoxy-ethoxy)-benzylidene]-2-thioxo-thiazolidin-4-one (which was obtained in Intermediate 37)(1.19 g, 5 mmol), rhodanine (0.67 g, 5 mmol) and piperidine (1.72 g, 20.2 mmol) in ethanol (50 mL) was refluxed for 2 hours. After cooling to room temperature hexanes (70 mL) were added and the solid which was formed was collected to give the title compound as a yellowish solid (1.4 9, 69%); 1H NMR (300 MHz, DMSO-d6) δ1.14(t, J=7.1 Hz, 6 H), 1.55-1.75(m, 6 H), 3.40-3.80 (m, 6 H), 3.85-3.95(m, 2 H), 4.20(d, J=5.2 Hz, 2 H), 4.82 (t, J=5.2 Hz, 1 H), 7.11 (d, J=7.6 Hz, 2 H), 7.57 (d, J=7.6 Hz, 2 H), 7.58(s, 1 H); MS (ES) m/z: 404.9 (MH+, 100%); HRMS Calcd. for C21H28N2O4S (M+): 404.1770. Found: 404.1780.

Workup

  1. temperaturewas refluxed for 2 hours
  2. additionwere added
  3. customthe solid which was formed
  4. customwas collected

Sources & evidence

ORD record
ord-f8e04b2d64a8414aae155985a4fcc51d
Source dataset
uspto-grants-2002_06
Patent number
US06410734B1

Reaction notes

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