Piperidine → (Z)-3-(5-(2,5-dimethoxybenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)propanoic acid

HRID 548085Notes

Reaction equation

HRID 548085 reaction equation
[O:1]=[C:2]1[CH2:6][S:5][C:4](=[S:7])[N:3]1[CH2:8][CH2:9][C:10]([OH:12])=[O:11].[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:16]=1[CH:17]=O.N1CCCCC1>C(O)C>[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:16]=1/[CH:17]=[C:6]1/[C:2](=[O:1])[N:3]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])[C:4](=[S:7])[S:5]/1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 667262,5-DimethoxybenzaldehydeHCID 814923-Thiazolidinepropionic acid, 4-oxo-2-thioxo-

Product 1

HCID 1201259(Z)-3-(5-(2,5-dimethoxybenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)propanoic acidYield 87.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(4-oxo-2-thioxothiazolidin-3-yl)propanoic acid (200 mg, 1 mmol), 2,5-dimethoxy benzaldehyde (168 mg, 1 mmol) and piperidine (0.3 mL) were combined in ethanol (3 mL) and irradiated in the microwave at 100° C. for 10 minutes. The reaction was cooled, the solid was collected by filtration, washed with ethyl acetate/hexanes (1/1) and recrystallized from ethanol to afford 85% yield of the title compound (309 mg, brown-orange solid). MS (M+H, 284); 1H NMR (400 MHz, DMSO-d6): δ, ppm: 2.57 (t, 2H)), 3.74 (s, J=6.8 Hz, 3H), 3.84 (s, 3H), 4.19 (t, 2H), 6.90 (s, 1H), 7.10 (s, 2H), 7.86 (s, 1H).

Workup

  1. customirradiated in the microwave at 100° C. for 10 minutes
  2. temperatureThe reaction was cooled
  3. filtrationthe solid was collected by filtration
  4. washwashed with ethyl acetate/hexanes (1/1)
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-f3ca375612884dbbbefa9af9408e3ca5
Source dataset
uspto-grants-2011_05
Patent number
US07939671B2

Reaction notes

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