Hydrochloric Acid → HCID 66973057, compound

HRID 1367183Notes

Reaction equation

HRID 1367183 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:14][CH2:13][C:12]([CH3:16])([CH3:15])[CH2:11][NH:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[H-].[Na+].Br[CH2:20][C:21]([O:23]C)=[O:22].[OH-:25].[Na+].Cl>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[N:10]([CH2:20][C:21]([OH:23])=[O:22])[C:11](=[O:25])[C:12]([CH3:16])([CH3:15])[CH2:13][CH2:14]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 60984Methyl bromoacetate2×HCID 66973470HCID 66973470, compound

Product 1

HCID 66973057HCID 66973057, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-(3,4-difluorophenyl)-5,5-dimethylpiperidine from Step A (47.0 mg, 0.209 mmol) in THF (2 mL) at 0° C. was added NaH (12.0 mg of a 60% dispersion in oil, 0.292 mmol). After 15 min, methyl bromoacetate (0.022 mL, 0.229 mmol) was added and the mixture was stirred at ambient temperature for 4 d, with additional methyl bromoacetate (0.022 mL, 0.229 mmol) added on the 2nd and 3rd days. Added NaOH (0.627 mL of a 1M solution) and the mixture was stirred at 50° C. for 16 h. The reaction mixture was acidified with 1 M HCl (5 mL) and extracted with EtOAc (3×10 mL). The combined organic extracts were washed with brine (5 mL), dried over Na2SO4, filtered, and concentrated in vacuo to provide the title compound. MS: m/z=284 (M+1).

Workup

  1. additionadded on the 2nd and 3rd days
  2. extractionextracted with EtOAc (3×10 mL)
  3. washThe combined organic extracts were washed with brine (5 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-17c36430c62040a6a18b815013abc30f
Source dataset
uspto-grants-2011_02
Patent number
US07893079B2

Reaction notes

Loading…