Hydrochloric Acid → HCID 19755335, compound

HRID 1588253Notes

Reaction equation

HRID 1588253 reaction equation
C([N:8]1[CH2:26][CH2:25][C:11]2([N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:14](=[O:22])[N:13]([CH3:23])[C:12]2=[O:24])[CH2:10][CH2:9]1)C1C=CC=CC=1.[ClH:27].[H][H]>CO.[Pd]>[ClH:27].[CH3:23][N:13]1[C:12](=[O:24])[C:11]2([CH2:10][CH2:9][NH:8][CH2:26][CH2:25]2)[N:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:14]1=[O:22]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4146666HCID 4146666, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19755335HCID 19755335, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 8-benzyl-3-methyl-1-phenyl-1,3,8-triazaspiro[4,5]decane-2,4-dione (470 mg, 1.3 mmol), from Step D, in methanol (100 mL) were added concentrated aqueous hydrochloric acid (0.12 mL, 1.4 mmol) and wet 20% palladium on carbon (0.47 g). The reaction vessel was pressurized with hydrogen (4 atmospheres) and shaken on a Parr apparatus at ambient temperature for 2 hours. The reaction mixture was then filtered sequentially through a paper filter and through a PTFE (polytetrafluoroethylene) filter membrane (0.45μ), rinsing with methanol. The filtrate was concentrated under reduced pressure and then the residue was dried to give 0.34 g (89% yield) of the title compound as a white solid, m.p.>330° C. (dec); MS (DCl/NH3) M/Z: 260 (M+H)+, 277 (M+NH4)+ ; 300 MHz 1H NMR (CDCl3) δ2.02 (td, J=5, 14 Hz, 2H), 2.31 (d, J=15 Hz, 2H), 3.08 (s, 3H), 3.34-3.43 (m, 2H), 3.72 (td, J=3, 12 Hz, 2H), 7.29-7.35 (m, 2H), 7.49-7.58 (m, 3H).

Workup

  1. filtrationThe reaction mixture was then filtered sequentially through a paper
  2. filtrationfilter and through a PTFE (polytetrafluoroethylene)
  3. filtrationfilter membrane (0.45μ)
  4. washrinsing with methanol
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was dried

Sources & evidence

ORD record
ord-45e62f3eb65f417a87bd80265e201e5a
Source dataset
uspto-grants-1993_06
Patent number
US05221675

Reaction notes

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