Hydrochloric Acid → 1-(3-Methylphenyl)-1,3,8-triazaspiro[4.5]decan-4-one

HRID 565600Notes

Reaction equation

HRID 565600 reaction equation
C([N:8]1[CH2:25][CH2:24][C:11]2([N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=3)[CH:14]=[N:13][C:12]2=[O:23])[CH2:10][CH2:9]1)C1C=CC=CC=1.Cl>[Pd].CO>[CH3:22][C:18]1[CH:17]=[C:16]([N:15]2[C:11]3([CH2:24][CH2:25][NH:8][CH2:9][CH2:10]3)[C:12](=[O:23])[NH:13][CH2:14]2)[CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 212683698-Benzyl-1-(3-methyl-phenyl)-1,3,8-triazaspiro[4,5]dec-2-en-4-one

Product 1

HCID 212683701-(3-Methylphenyl)-1,3,8-triazaspiro[4.5]decan-4-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 8-benzyl-1-(3-methylphenyl)-1,3,8-triazaspiro[4.5]dec-2-en-4-one (1.64 g, 4.9 mmol) and 10% palladium on charcoal (0.8 g) in a mixture of methanol (100 mL) and methanol saturated with anhydrous hydrochloride gas (5 mL) was shaken in a Parr hydrogenator at 55 psi for 24 h. The resultant mixture was filtered through a plug of Celite, and the filtrate concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with a 1:1 mixture of 10% methanol in chloroform and chloroform saturated with ammonia gas. Collection and concentration of appropriate fractions provide the title compound.

Workup

  1. filtrationThe resultant mixture was filtered through a plug of Celite
  2. concentrationthe filtrate concentrated under vacuum
  3. additionThe residue was subjected to column chromatography on silica gel eluting with a 1:1 mixture of 10% methanol in chloroform and chloroform saturated with ammonia gas
  4. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-87e8a7ab77704e73a898e6d0a8eb358e
Source dataset
uspto-grants-2001_01
Patent number
US06172076B2

Reaction notes

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