Hydrochloric Acid → HCID 69082599, compound

HRID 594413Notes

Reaction equation

HRID 594413 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH:11]1[N:16]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=2)[C:15](=[O:29])[CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12]1.Cl.O1CCOCC1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH:11]1[N:16]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]([F:27])([F:28])[F:26])=[CH:20][CH:19]=2)[C:15](=[O:29])[CH2:14][NH:13][CH2:12]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 69095725HCID 69095725, compound

Product 1

HCID 69082599HCID 69082599, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A cooled (0° C.) solution of tert-butyl 3-(2,6-dimethoxyphenyl)-5-oxo-4-(4-(trifluoromethoxy)-benzyl)piperazine-1-carboxylate (540 mg; 1.05 mmol) in anh. DCM (10 ml) was treated dropwise with 4 M HCl in dioxane (4.00 ml; 16.00 mmol), and the resulting mixture was further stirred at rt, under nitrogen, for 16 h. The reaction mixture was concentrated to dryness under reduced pressure, the resulting residue was dissolved in DCM, and washed successively with 1 M aq. NaOH, aq. sat. NaHCO3, and brine. The organic layer was dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=10/1) afforded 6-(2,6-dimethoxyphenyl)-1-(4-(trifluoromethoxy)benzyl)piperazin-2-one as an orange oil. LC-MS (conditions D): tR=0.85 min.; [M+H]+: 411.13 g/mol.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  2. dissolutionthe resulting residue was dissolved in DCM
  3. washwashed successively with 1 M aq. NaOH, aq. sat. NaHCO3, and brine
  4. dry with materialThe organic layer was dried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customPurification by FC (DCM/MeOH=10/1)

Sources & evidence

ORD record
ord-9e2310c1c6324a7aaddff89a5159827e
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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