1-Benzylpiperazine → HCID 42598821, compound

HRID 875264Notes

Reaction equation

HRID 875264 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CC(S(O[CH2:25][C:26]2([OH:43])[C:30](=[O:31])[O:29][C@H:28]3[C:32]4[C@@:37]([CH3:40])([CH2:38][CH2:39][C:27]23[OH:42])[CH2:36][CH2:35][CH2:34][C:33]=4[CH3:41])(=O)=O)=CC=1>C(O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:25][C:26]2([OH:43])[C:30](=[O:31])[O:29][C@H:28]3[C:32]4[C@@:37]([CH3:40])([CH2:38][CH2:39][C:27]23[OH:42])[CH2:36][CH2:35][CH2:34][C:33]=4[CH3:41])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 759941-BenzylpiperazineHCID 42598818HCID 42598818, compound

Product 1

HCID 42598821HCID 42598821, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Benzyl piperazine (190 mg, 1.078 mmol) was added to the solution of compound of example 5 (470 mg, 1.078 mmol) in ethanol (15 mL), and stirred at 50° C. under nitrogen atmosphere for 6 hours. The reaction mixture was concentrated, and dissolved in water (25 mL) and was extracted using ethyl acetate (3×50 mL). Ethyl acetate layer was washed with water and brine, dried over sodium sulfate. Solvent was removed and crude product was purified by column chromatography (silica gel, using 12.5% ethyl acetate in petroleum ether). Semi-pure product was crystallized using ethyl acetate/petroleum ether to obtain the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved in water (25 mL)
  3. extractionwas extracted
  4. washEthyl acetate layer was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customSolvent was removed
  7. customcrude product was purified by column chromatography (silica gel, using 12.5% ethyl acetate in petroleum ether)
  8. customSemi-pure product was crystallized

Sources & evidence

ORD record
ord-69dd430a7f784706abd793d749e9f245
Source dataset
uspto-grants-2015_03
Patent number
US08981131B2

Reaction notes

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