Hydrochloric Acid → 2-(2-Chlorophenyl)-1,3-diazaspiro[4.4]non-1-en-4-one

HRID 1890705Notes

Reaction equation

HRID 1890705 reaction equation
[NH2:1][C:2]([C:4]1([NH:9][C:10](=O)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[CH2:8][CH2:7][CH2:6][CH2:5]1)=[O:3].[OH-].[Na+].Cl>CO.C(Cl)Cl>[Cl:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:10]1[NH:1][C:2](=[O:3])[C:4]2([CH2:8][CH2:7][CH2:6][CH2:5]2)[N:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58550576N-[1-(Aminocarbonyl)cyclopentyl]-2-chlorobenzamide

Product 1

HCID 585505832-(2-Chlorophenyl)-1,3-diazaspiro[4.4]non-1-en-4-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

Into a solution of N-[1-(aminocarbonyl)cyclopentyl]-2-chlorobenzamide from Step A (0.51 g, 1.912 mmol) in methanol (10 mL) was added NaOH (1.15 mL, 5 N). This solution was heated at 90° C. for 2.5 h. After allowing the reaction mixture to cool, the bulk of the solvent was removed in vacuo to give a residue, which was then neutralized by the addition of 1 N HCl and diluted with DCM. The layers were separated and the aqueous layer was extracted with an additional volume of DCM. The combined organics were dried over sodium sulfate, filtered, and concentrated in vacuo to yield the title compound as a white solid. MS: m/z=249 (M+1).

Workup

  1. temperatureto cool
  2. customthe bulk of the solvent was removed in vacuo
  3. customto give a residue, which
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with an additional volume of DCM
  6. dry with materialThe combined organics were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-beb8a6f2532d410daaede95d678130b1
Source dataset
uspto-grants-2013_08
Patent number
US08507477B2

Reaction notes

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