Hydrochloric Acid → HCID 46938190, compound

HRID 1873708Notes

Reaction equation

HRID 1873708 reaction equation
C([N:8]1[CH2:13][C@@H:12]([CH2:14][F:15])[C@@H:11]([OH:16])[C@H:10]([O:17]CC2C=CC=CC=2)[CH2:9]1)C1C=CC=CC=1.[ClH:25]>CCO>[ClH:25].[F:15][CH2:14][C@@H:12]1[CH2:13][NH:8][CH2:9][C@@H:10]([OH:17])[C@@H:11]1[OH:16]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66734926HCID 66734926, compound

Product 1

HCID 46938190HCID 46938190, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 7 (7.5 g, 22.8 mmol) in EtOH (150 mL) was added 5N HCl in 2-PrOH (7 mL). The solution was evaporated in vacuo, then co-evaporated 2× more with EtOH. The resulting material was dissolved in EtOH (100 mL) and the resulting solution was hydrogenated overnight with Pd(OH)2 at 50 psi. The catalyst was removed by filtration and the filtrate was evaporated in vacuo. The residue was triturated with acetone and a pale yellow solid was collected. The resulting solid was recrystallized from EtOH to give the title compound as an off-white solid mp 200-202° C. 1H NMR DMSO d6 consistent with previous spectra.

Workup

  1. customThe solution was evaporated in vacuo
  2. dissolutionThe resulting material was dissolved in EtOH (100 mL)
  3. customThe catalyst was removed by filtration
  4. customthe filtrate was evaporated in vacuo
  5. customThe residue was triturated with acetone
  6. customa pale yellow solid was collected
  7. customThe resulting solid was recrystallized from EtOH

Sources & evidence

ORD record
ord-64f387747f7c49aa937232d47d3eeca3
Source dataset
uspto-grants-2012_11
Patent number
US08304429B2

Reaction notes

Loading…