Hydrochloric Acid → HCID 9970871, compound

HRID 1765999Notes

Reaction equation

HRID 1765999 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:10][C@H:9]2[CH3:33])[CH:5]=[CH:4][C:3]=1[C:34]([F:37])([F:36])[F:35].Cl.O>CCO>[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]2[CH3:33])[CH:5]=[CH:4][C:3]=1[C:34]([F:37])([F:35])[F:36]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 21109178HCID 21109178, compound

Product 1

HCID 9970871HCID 9970871, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 1-(6-chloro-5-trifluoromethyl-pyridin-2-yl)-2-(R)-methyl-4-trityl-piperazine (from Step 1 above; 5.70 g, 10.9 mmol) in EtOH (70 mL) was heated to 80° C. Aqueous HCl (4 M; 6 mL) was added and the mixture was heated in an open vessel for one hour. To the clear solution was water added (100 mL) and the precipitate was filtered off. The solvent from the filtrate was evaporated down to about 10 mL, the crystals were filtered off and the evaporation continued down to 3 mL and another portion of slightly pinkish crystals were filtered off. The combined crystal fractions were taken up between alkaline water (NaOH)/CHCl3. The aqueous phase was washed twice with CHCl3 and the combined, dried (MgSO4), organic phases were evaporated at reduced pressure to give a light yellow oil (1.75 g, 69%). A NOE between the methylene protons at C-2 in the piperazine ring and the C3-hydrogen in the pyridine ring was observed. Purity 99% (HPLC). Fragmenting MS analysis supports the stated structure. HRMS m/z calcd for C11H13ClF3N3 (M)+ 279.0750. found 279.0744.

Workup

  1. temperaturethe mixture was heated in an open vessel for one hour
  2. additionadded (100 mL)
  3. filtrationthe precipitate was filtered off
  4. customThe solvent from the filtrate was evaporated down to about 10 mL
  5. filtrationthe crystals were filtered off
  6. customthe evaporation
  7. filtrationanother portion of slightly pinkish crystals were filtered off
  8. washThe aqueous phase was washed twice with CHCl3
  9. dry with materialdried (MgSO4), organic phases
  10. customwere evaporated at reduced pressure

Sources & evidence

ORD record
ord-4b004bc20db14c2ba1e50c7f9bcd3264
Source dataset
uspto-grants-2007_06
Patent number
US07229997B2

Reaction notes

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