Hydrochloric Acid → 4-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-3-methyl-1-pent-4-enyl-piperazin-2-one

HRID 559327Notes

Reaction equation

HRID 559327 reaction equation
Cl.C(O[C:7]([N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH:18]=[CH2:19])[C:11](=[O:20])[CH:10]1[CH3:21])=[O:8])(C)(C)C.CN1CCOCC1.[Cl:29][C:30]1[CH:31]=[C:32]([CH:38]=[CH:39][C:40]=1[Cl:41])[CH:33]=[CH:34]C(O)=O.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>>[Cl:29][C:30]1[CH:31]=[C:32](/[CH:33]=[CH:34]/[C:7]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH:18]=[CH2:19])[C:11](=[O:20])[CH:10]2[CH3:21])=[O:8])[CH:38]=[CH:39][C:40]=1[Cl:41]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 79724-Methylmorpholine2×HCID 145483-(3,4-Dichlorophenyl)prop-2-enoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 669990522-Methyl-3-oxo-4-pent-4-enyl-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 669992764-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-3-methyl-1-pent-4-enyl-piperazin-2-oneYield 86.1%

Procedure

Hydrogen chloride solution (4 M in 1,4-dioxane, 8 ml) was added to a solution of 2-methyl-3-oxo-4-pent-4-enyl-piperazine-1-carboxylic acid tert-butyl ester (200 mg, 0.71 mmol). The reaction mixture was stirred at room temperature for 3.5 h, then volatile material was removed by rotary evaporation. The residue was taken up in dichlormethane (10 ml), treated with 4-methylmorpholine (358 mg, 3.54 mmol), and the mixture obtained concentrated in vacuo. The residue was taken up in N,N-dimethylformamide (8 ml), then 4-methylmorpholine (358 mg, 3.54 mmol), 3,4-dichlorocinnamic acid (161 mg, 0.71 mmol), and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluoro-phosphate (404 mg, 1.06 mmol) were added. The solution was stirred at room temperature for 48 h, then the mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2; heptane-ethyl acetate gradient) produced the title compound (233 mg, 86%). Light yellow oil, MS (ISP)=381.2 (M+H)+.

Workup

  1. customvolatile material was removed by rotary evaporation
  2. customthe mixture obtained
  3. concentrationconcentrated in vacuo
  4. stirringThe solution was stirred at room temperature for 48 h
  5. customthe mixture was partitioned between water and ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-598dbb35ea124b8b9d04ab86e094747d
Source dataset
uspto-grants-2011_11
Patent number
US08063042B2

Reaction notes

Loading…