Hydrochloric Acid → [(4-Fluoro-phenyl)-methyl-amino]-phenyl-acetic acid hydrochloride

HRID 1044036Notes

Reaction equation

HRID 1044036 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:21])[CH:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:10]([O:12]CC)=[O:11])=[CH:4][CH:3]=1.O.[OH-].[Li+].[ClH:25]>C1COCC1.O>[ClH:25].[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:21])[CH:9]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 58556946Ethyl 2-((4-fluorophenyl)(methyl)amino)-2-phenylacetate

Product 1

HCID 67124664[(4-Fluoro-phenyl)-methyl-amino]-phenyl-acetic acid hydrochlorideYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-((4-fluorophenyl)(methyl)amino)-2-phenylacetate (I5) (0.59 g, 2.05 mmol) was dissolved in a mixture THF (10 ml) and water (10 ml), and lithium hydroxide hydrate (0.26 g, 6.14 mmol) was added. The reaction was stirred at room temperature for 3.5 hours and then at 70° C. for 24 hours. 3N HCl was added till pH was about 1, and the mixture was evaporated. Water (15 ml) was added, and the residue was triturated obtaining a pale brown suspension that was filtered on a buckner funnel washing with water and then with acetonitrile. The solid was dried under vacuum at 40° C. overnight to obtain intermediate I6 (0.44 g, 72% yield).

Workup

  1. additionwas added
  2. waitat 70° C. for 24 hours
  3. customthe mixture was evaporated
  4. additionWater (15 ml) was added
  5. customthe residue was triturated
  6. customobtaining a pale brown suspension that
  7. filtrationwas filtered on a buckner funnel
  8. washwashing with water
  9. customThe solid was dried under vacuum at 40° C. overnight
  10. customto obtain intermediate I6 (0.44 g, 72% yield)

Sources & evidence

ORD record
ord-595b35f095614cc3baa3cbad86f43b53
Source dataset
uspto-grants-2013_10
Patent number
US08563577B2

Reaction notes

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