Hydrochloric Acid → 1-[4-(2-methoxyphenyl)-1-piperazinyl]-2-Propen-1-one

HRID 1016644Notes

Reaction equation

HRID 1016644 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].Cl.[CH3:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(N(CC)CC)C.Cl>ClCCl>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[CH2:20][CH2:19][N:18]([C:1](=[O:4])[CH:2]=[CH2:3])[CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 9899402N-(2-Methoxyphenyl)piperazine hydrochloride

Product 1

HCID 184070531-[4-(2-methoxyphenyl)-1-piperazinyl]-2-Propen-1-oneYield 22.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acryloyl chloride (10.6 mL, 11.8 g, 0.13 mol) was added dropwise to a stirred, cooled (0° C.) mixture of 1-(2-methoxyphenyl)piperazine hydrochloride (15 g, 66 mmol) and triethylamine (27.3 g, 19.8 g, 0.20 mol) in dichloromethane and the mixture was stirred at room temperature for 2 h. The mixture was poured into hydrochloric acid (1M) and extracted with dichloromethane. The combined organic fractions were washed with aqueous sodium hydrogen carbonate (saturated), dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with isohexane/EtOAc (40:60 increasing to 20:80), to give the title compound as a pale yellow oil (3.6 g, 22%). 1H NMR (360 MHz, CDCl3) δ 7.04 (1H, m), 6.95-6.84 (3H, m), 6.61 (1H, dd, J 16.8, 10.6 Hz), 6.32 (1H, dd, J 16.8, 1.8 Hz), 5.72 (1H, dd, J 10.6, 1.8 Hz), 3.94-3.84 (2H, m), 3.89 (3H, s), 3.74 (2H, m), and 3.06 (4H, m). m/z (ES+) 247 (M+1).

Workup

  1. temperaturecooled
  2. extractionextracted with dichloromethane
  3. washThe combined organic fractions were washed with aqueous sodium hydrogen carbonate (saturated)
  4. dry with materialdried (MgSO4)
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by flash column chromatography on silica gel
  7. washeluting with isohexane/EtOAc (40:60 increasing to 20:80)

Sources & evidence

ORD record
ord-76bd5ff0dd4049948ad1e188d010421a
Source dataset
uspto-grants-2002_11
Patent number
US06476045B2

Reaction notes

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