Hydrochloric Acid → Propiophenone, 3-(4-phenyl-1-piperazinyl)-

HRID 1367696Notes

Reaction equation

HRID 1367696 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].Cl.[C:11]1([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl.[CH2:24]=O>C(O)C>[C:4]1([C:1](=[O:3])[CH2:2][CH2:24][N:20]2[CH2:21][CH2:22][N:17]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:18][CH2:19]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 7410AcetophenoneHCID 751641-Phenylpiperazinium chloride

Product 1

HCID 213313Propiophenone, 3-(4-phenyl-1-piperazinyl)-Yield 80.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A well-stirred mixture of acetophenone (17) (3.40 mL, 29.0 mmol), 1-phenylpiperazine hydrochloride (18) (4.48 g, 22.5 mmol), and 0.05 mL of concentrated HCl in absolute ethanol (35 mL) was heated under N2 at reflux conditions. Paraformaldehyde (1.00 g, 33.3 mmol) was added in four equal portions over 40 minutes. The reaction mixture was further refluxed for 6 hours. The solution was then cooled and poured onto crushed ice. The solid was separated by filtration, dried, and re-crystallized using a small amount of aqueous ethanol (<10 mL). The solution was allowed to cool overnight and yielded 5.32 g the desired product 19 (18.1 mmol, 62%) as a white, yellow crystal. 1H-NMR (CDCl3): δ 8.03 (2 H, d, J=7.24 Hz), 7.63 (1 H, t, J=7.37, 7.42 Hz), 7.50 (2H, t, J=7.87, 7.35 Hz), 7.31 (2H, m), 6.97 (3H, m), 3.89 (2H, t, J=6.89, 6.72 Hz), 3.62 (8H, m), 3.10 (2H, m). 13C-NMR (CDCl3): δ 195.99, 149.27, 135.41, 134.24, 129.51, 128.37, 122.00, 117.43, 52.36, 51.97, 46.91, 33.14. Melting Point: 182-185° C.

Workup

  1. temperaturewas heated under N2
  2. temperatureat reflux conditions
  3. temperatureThe reaction mixture was further refluxed for 6 hours
  4. temperatureThe solution was then cooled
  5. additionpoured
  6. customonto crushed ice
  7. customThe solid was separated by filtration
  8. customdried
  9. customre-crystallized
  10. temperatureto cool overnight

Sources & evidence

ORD record
ord-658e36ae12a04ac89f866180163e15cb
Source dataset
uspto-grants-2011_02
Patent number
US07893261B2

Reaction notes

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