Sodium Hydroxide → HCID 58996699, compound

HRID 1592738Notes

Reaction equation

HRID 1592738 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20][NH2:21])[CH2:10][CH2:9]1)(OC(C)(C)C)=O.CCN(C(C)C)C(C)C.[CH3:31][C:32]([CH3:37])([CH3:36])[C:33](Cl)=[O:34].[OH-].[Na+]>C(Cl)Cl.C(OCC)(=O)C.C(O)(C(F)(F)F)=O>[CH3:31][C:32]([CH3:37])([CH3:36])[C:33]([NH:21][CH2:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[N:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)=[O:34]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 62493Pivaloyl chlorideHCID 81531DiisopropylethylamineHCID 4961274Tert-butyl 4-[2-(aminomethyl)phenyl]piperazine-1-carboxylate

Product 1

HCID 58996699HCID 58996699, compoundYield 85.3%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

1-Boc-4-(2-Aminomethyl-phenyl)-piperazine (0.75 g, 2.6 mmol) was dissolved in methylene chloride (20 mL). DIPEA (2.3 mL, 13 mmol) was added, and the mixture was cooled to about 0° C. The solution was treated with trimethylacetyl chloride (0.28 g, 0.28 mL, 2.3 mmol) and stirred for about 1 hour at 0° C. The solution was warmed to r.t. and stirred overnight. The mixture was diluted with ethyl acetate (400 mL), washed with water (60 mL), saturated aqueous sodium bicarbonate (60 mL) and brine (60 mL) and then dried over anhydrous sodium sulfate. The solution was concentrated under reduced pressure and purified via silica gel chromatography (80% ethyl acetate in hexanes) to afford a clear oil, which was subsequently stirred in neat TFA (5 mL) for about 1 hours. The solvent was evaporated under reduced pressure and the residue taken up in water (30 mL). Sodium hydroxide (1 g, 25 mmol) and ethyl acetate (30 mL) were added, and the mixture was stirred for about 45 minutes. The organic phase was collected and the aqueous phase was extracted with ethyl acetate (60 mL). The combined organic fractions were washed with water (45 mL) and brine (30 mL) and then dried over anhydrous sodium sulfate. Concentration under reduced pressure afforded the title compound (0.54 g, 75%) as a clear oil.

Workup

  1. temperatureThe solution was warmed to r.t.
  2. stirringstirred overnight
  3. washwashed with water (60 mL), saturated aqueous sodium bicarbonate (60 mL) and brine (60 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe solution was concentrated under reduced pressure
  6. custompurified via silica gel chromatography (80% ethyl acetate in hexanes)
  7. customto afford a clear oil, which
  8. customThe solvent was evaporated under reduced pressure
  9. stirringthe mixture was stirred for about 45 minutes
  10. customThe organic phase was collected
  11. extractionthe aqueous phase was extracted with ethyl acetate (60 mL)
  12. washThe combined organic fractions were washed with water (45 mL) and brine (30 mL)
  13. dry with materialdried over anhydrous sodium sulfate
  14. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-e55a297f47a24e0c9c22e7a4ce56512e
Source dataset
uspto-grants-2007_11
Patent number
US07291619B2

Reaction notes

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