Piperazine → HCID 67504085, compound

HRID 574290Notes

Reaction equation

HRID 574290 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>C(O)(C)C>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][O:12][C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:6]=2[N:5]=[CH:4][CH:3]=[C:2]3[N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 67504897HCID 67504897, compound

Product 1

HCID 67504085HCID 67504085, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of compound 23 (4.70 g, 15.68 mmol) and piperazine (13.63 g, 158.23 mmol) in isopropanol (30 mL) was refluxed for 46 hours with stirring. Isopropanol was evaporated under vacuo and the reaction mixture was made alkaline using saturated NaHCO3 solution. The aqueous layer was extracted with CH2Cl2 (3×100 mL), dried over Na2SO4, concentrated under vacuo to afford 5.32 g (97%) of compound 24, which was used for the next reaction without further purification. 1H NMR (400 MHz, CDCl3) δ ppm 1.73 (bs, 1H), 2.80-3.44 (m, 8H), 3.80 (s, 3H), 5.36 (s, 2H), 6.82-6.94 (m, 2H), 6.99 (d, 1H, J=8 Hz), 7.23-7.35 (m, 1H), 7.44 (d, 2H, J=8.4 Hz), 7.58 (d, 1H, J=8 Hz), 8.76-8.82 (m, 1H).

Workup

  1. temperaturewas refluxed for 46 hours
  2. customIsopropanol was evaporated under vacuo
  3. extractionThe aqueous layer was extracted with CH2Cl2 (3×100 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-12298f1785e94fc09a3c86203324e26a
Source dataset
uspto-grants-2015_05
Patent number
US09034877B2

Reaction notes

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