Dimethylformamide → Piperidin-1-yl-acetic acid

HRID 1989873Notes

Reaction equation

HRID 1989873 reaction equation
[C:1]([O-:4])([O-])=[O:2].[Na+].[Na+].Br[CH:8]([C:13]1C=CC=[CH:15][CH:14]=1)[C:9](OC)=O.[CH3:19][N:20](C=O)C>>[N:20]1([CH2:19][C:1]([OH:4])=[O:2])[CH2:15][CH2:14][CH2:13][CH2:8][CH2:9]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 137806Benzeneacetic acid, alpha-bromo-, methyl ester

Product 1

HCID 201097Piperidin-1-yl-acetic acid

Procedure

A mixture of intermediate (40) (0.0084 mol) and Na2CO3 (0.01 mol) in DMF (150 ml) was stirred. Methyl 2-bromo-2-phenylacetate (0.01 mol) was added dropwise. The mixture was stirred overnight. The solvent was evaporated. The residue was dissolved in DCM. The organic layer was separated, washed, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: DCM 100%). The pure fractions were collected and the solvent was evaporated. The residue was triturated in DIPE. The precipitate was filtered off and dried, yielding 2.79 g of 1-piperidineacetic acid, 4-[4-[([1,1′-biphenyl]-2-ylcarbonyl)amino]phenyl]-α-phenyl-, methyl ester (intermediate 41).

Workup

  1. stirringThe mixture was stirred overnight
  2. customThe solvent was evaporated
  3. dissolutionThe residue was dissolved in DCM
  4. customThe organic layer was separated
  5. washwashed
  6. customdried
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was purified by column chromatography over silica gel (eluent: DCM 100%)
  10. customThe pure fractions were collected
  11. customthe solvent was evaporated
  12. customThe residue was triturated in DIPE
  13. filtrationThe precipitate was filtered off
  14. customdried

Sources & evidence

ORD record
ord-c626376468c74225944fb9810361423a
Source dataset
uspto-grants-2010_01
Patent number
US07642378B2

Reaction notes

Loading…