HCID 45789390, compound → 1-(4-Fluorophenyl)-1,3,8-triazaspiro(4.5)decan-4-one

HRID 458142Notes

Reaction equation

HRID 458142 reaction equation
C([N:8]1[CH2:25][CH2:24][C:11]2([N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:14]=[N:13][C:12]2=[O:23])[CH2:10][CH2:9]1)C1C=CC=CC=1>CO.C(O)(=O)C.[Pd]>[F:22][C:19]1[CH:20]=[CH:21][C:16]([N:15]2[C:11]3([CH2:10][CH2:9][NH:8][CH2:25][CH2:24]3)[C:12](=[O:23])[NH:13][CH2:14]2)=[CH:17][CH:18]=1

Participants

5

Reactant 1

HCID 45789390HCID 45789390, compound

Product 1

HCID 939151-(4-Fluorophenyl)-1,3,8-triazaspiro(4.5)decan-4-one

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 81 g 8-benzyl-1-(4-fluoro-phenyl)-1,3,8-triaza-spiro[4.5]dec-2-en-4-one in 960 ml methanol and 24 ml acetic acid were added 21.2 g 10% Pd on charcoal and stirred for 16 h under a hydrogen atmosphere at ambient temperature. The reaction mixture was filtered, concentrated, diluted with 100 ml water, made alkaline with sat NaHCO3 solution and extracted with dichloromethane. The combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated. The residue, 23 g crude product, was crystallised from AcOEt: 6.6 g 1-(4-fluoro-phenyl)-1,3,8-triaza-spiro[4.5]decan-4-one as colorless crystals: MS (ISP): 250.2 MH+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. additiondiluted with 100 ml water
  4. extractionextracted with dichloromethane
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue, 23 g crude product, was crystallised from AcOEt

Sources & evidence

ORD record
ord-a9f306720b804908b8d6816f71cc9cef
Source dataset
uspto-grants-2007_03
Patent number
US07189850B2

Reaction notes

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