Hydrochloric Acid → HCID 47283403, compound

HRID 2364839Notes

Reaction equation

HRID 2364839 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.[OH-].[Na+].Cl[C:20]([O:22][CH3:23])=[O:21].Cl>O1CCOCC1.CCOC(C)=O>[CH3:23][O:22][C:20]([N:14]1[CH2:15][CH2:16][N:11]([C:3]2[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=2[F:1])[CH2:12][CH2:13]1)=[O:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 14798Sodium HydroxideHCID 27830661-(2-fluoro-4-nitrophenyl)piperazine

Product 1

HCID 47283403HCID 47283403, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of Example 119A (4.0 g, 17.76 mmol) in dioxane (40 mL) at 0° C. was added 2 M NaOH (29.3 mL, 58.6 mmol) followed by dropwise addition of methyl chloroformate (2.75 mL, 35.5 mmol). The solution was warmed to room temperature and stirred for 2 h. Diluted with EtOAc and added 1 N HCl until all solid had dissolved, separated the phases and washed the organic phase with 1 N HCl, H2O, brine, dried (Na2SO4), filtered and removed solvent in vacuo to give the title compound (4.69 g, 16.56 mmol, 93%). 1H NMR (400 MHz, CDCl3) δ ppm 3.20-3.31 (m, 4H) 3.62-3.71 (m, 4H) 3.75 (s, 3H) 6.92 (t, J=8.8 Hz, 1H) 7.93 (dd, J=12.9, 2.6 Hz, 1H) 7.98-8.02 (m, 1H). MS (ESI) m/z 284 (M+H)+.

Workup

  1. dissolutionhad dissolved
  2. customseparated the phases
  3. washwashed the organic phase with 1 N HCl, H2O, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customremoved solvent in vacuo

Sources & evidence

ORD record
ord-a4f13dbb07a249cc84ba52332cba55e5
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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