Hydrochloric Acid → 1-[4-(4-Oxo-2-thioxo-thiazolidin-5-ylidenemethyl)-phenyl]-piperidin-4-one

HRID 1061217Notes

Reaction equation

HRID 1061217 reaction equation
O1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:24]=[CH:23][C:14]([CH:15]=[C:16]4[S:20][C:19](=[S:21])[NH:18][C:17]4=[O:22])=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)[O:4]CC1.Cl.[OH-].[NH4+]>>[O:22]=[C:17]1[C:16](=[CH:15][C:14]2[CH:13]=[CH:12][C:11]([N:8]3[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]3)=[CH:24][CH:23]=2)[S:20][C:19](=[S:21])[NH:18]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 854336695-[4(1,4-Dioxa-8-aza-spiro[4,5]dec-8-yl)-benzylidene]-2-thioxothiazolidin-4-one

Product 1

HCID 731782011-[4-(4-Oxo-2-thioxo-thiazolidin-5-ylidenemethyl)-phenyl]-piperidin-4-oneYield 89.2%

Procedure

5-[4(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-benzylidene]-2-thioxothiazolidin-4-one (which was obtained in Example 33) (0.9 g, 2.5 mmol) was treated with concentrated hydrochloric acid (25 mL) at room temperature. After 15 hours ˜28% ammonium hydroxide (NH4OH) was added dropwise and the precipitate was collected by filtration, and dried over phosphorus pentoxide (P2O5) to give the title compound as a red solid (0.71 g, 89%); 1H NMR (300 MHz, DMSO-d6) δ 2.46 (t, J=6.1 Hz, 4H), 3.79 (t, J=6.1 Hz, 4H), 7.11 (d, J=9.0 Hz, 2H), 7.48 (d, J=9.0 Hz, 2H), 7.56 (s, 1H); MS (ES) m/z: 316.9 (M−H)−; HRMS Calcd. C15H14N2O2S2 (M+): 318.0497. Found: 318.0502.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. dry with materialdried over phosphorus pentoxide (P2O5)

Sources & evidence

ORD record
ord-3234b95baf1f49f7bdfe0418ee4c5fec
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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