Benzoyl chloride → HCID 58996626, compound

HRID 1592739Notes

Reaction equation

HRID 1592739 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.[C:31](Cl)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(Cl)Cl.C(OCC)(=O)C.C(O)(C(F)(F)F)=O>[C:31]([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:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

7

Reactant 3

HCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 4961274Tert-butyl 4-[2-(aminomethyl)phenyl]piperazine-1-carboxylate

Product 1

HCID 58996626HCID 58996626, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

1-Boc-4-(2-Aminomethyl-phenyl)-piperazine (0.47 g, 1.6 mmol) was dissolved in methylene chloride (20 mL). DIPEA (1.5 mL, 8.5 mmol) was added, and the mixture was cooled to about 0° C. The mixture was treated with benzoyl chloride (0.20 g, 0.16 mL, 1.4 mmol). The resulting mixture was stirred for about 1 hour at 0° C., and then warmed to r.t. and stirred overnight. The mixture was diluted with ethyl acetate (500 mL), washed with water (45 mL), saturated aqueous sodium bicarbonate (45 mL) and brine (45 mL) and then dried over anhydrous sodium sulfate. The solution was concentrated under reduced pressure and purified via silica gel chromatography (50% ethyl acetate in hexanes) to afford a clear oil, which was subsequently stirred in neat TFA (5 mL) for about 1 hour. The solvent was evaporated under reduced pressure to afford the title compound as a clear oil (0.30 g, 100%).

Workup

  1. temperaturewarmed to r.t.
  2. stirringstirred overnight
  3. washwashed with water (45 mL), saturated aqueous sodium bicarbonate (45 mL) and brine (45 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe solution was concentrated under reduced pressure
  6. custompurified via silica gel chromatography (50% ethyl acetate in hexanes)
  7. customto afford a clear oil, which
  8. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9deb50143dc74ee78af58b37a1e50c27
Source dataset
uspto-grants-2007_11
Patent number
US07291619B2

Reaction notes

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