Hydrochloric Acid → HCID 12070446, compound

HRID 983660Notes

Reaction equation

HRID 983660 reaction equation
[CH3:1][N:2]1C[CH2:6][CH2:5][CH2:4][C:3]1=O.Cl.[C:10](=[O:13])([O-])[O-:11].[Na+].[Na+].[Br:16][C:17]1[C:18](F)=[CH:19][CH:20]=[C:21]([CH:24]=1)[CH:22]=[O:23]>[OH-].[Na+].CS(C)=O.C(OC(C)C)(C)C>[Br:16][C:17]1[CH:18]=[CH:19][C:20]([N:2]([CH2:3][CH2:4][CH2:5][CH2:6][C:10]([OH:11])=[O:13])[CH3:1])=[C:21]([CH:22]=[O:23])[CH:24]=1

Participants

8

Reactant 4

HCID 313Hydrochloric Acid2×HCID 10340Sodium CarbonateHCID 13603N-Methyl-2-piperidoneHCID 1736043-Bromo-4-fluorobenzaldehyde

Product 1

HCID 12070446HCID 12070446, compoundYield 57.4%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 7914Diisopropyl EtherSolventHCID 14798Sodium HydroxideSolvent

Procedure

A suspension of 1-methyl-2-piperidone (5.0 g) in 4N sodium hydroxide (22.1 ml) was heated and stirred for 8.5 hours under reflux. After the suspension was cooled to room temperature, conc. hydrochloric acid (7.4 ml) was added. A solution of sodium carbonate (9.4 g) and 5-bromo-4-fluorobenzaldehyde (4.5 g) in DMSO (74 ml) was added, and the resulting mixture was stirred for 1.5 hours under reflux. The mixture was allowed to cool to room temperature, and adjusted to pH of about 3.3 with 6N hydrochloric acid. After extraction with ethyl acetate, the organic layer was washed with saturated salt water, dried over anhydrous sodium sulfate, and concentrated. The precipitated crystal obtained was redissolved in isopropylether [IPE] (20 ml) under heating, and the solution was allowed to cool to room temperature, and stirred for 1 hour at 0° C. The crystal obtained was filtered and washed with IPE. Drying under reduced pressure (40° C., 1 hour) gave yellow crystal of 5-(4-bromo-2-formyl-N-methylanilino)pentanoic acid (4.0 g, yield 57%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. stirringthe resulting mixture was stirred for 1.5 hours
  4. temperatureunder reflux
  5. temperatureto cool to room temperature
  6. extractionAfter extraction with ethyl acetate
  7. washthe organic layer was washed with saturated salt water
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated
  10. customThe precipitated crystal obtained
  11. temperatureunder heating
  12. temperatureto cool to room temperature
  13. stirringstirred for 1 hour at 0° C
  14. customThe crystal obtained
  15. filtrationwas filtered
  16. washwashed with IPE
  17. customDrying under reduced pressure (40° C., 1 hour)

Sources & evidence

ORD record
ord-9fb965eb54474b8fa871d4d83622f734
Source dataset
uspto-grants-2005_03
Patent number
US06864367B2

Reaction notes

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