Hydrochloric Acid → HCID 86624303, compound

HRID 1013060Notes

Reaction equation

HRID 1013060 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[C:22]([O-:25])(O)=[O:23].[Na+].Cl[S:28]([C:31]1[CH:36]=[CH:35][C:34]([CH:37]=[CH:38]C(O)=O)=[CH:33][CH:32]=1)(=[O:30])=[O:29].Cl>O1CCOCC1.O>[F:21][C:18]1[CH:19]=[CH:20][C:15]([CH:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[N:9]2[CH2:10][CH2:11][N:12]([S:28]([C:31]3[CH:36]=[CH:35][C:34]([C:37](=[CH2:38])[C:22]([OH:25])=[O:23])=[CH:33][CH:32]=3)(=[O:30])=[O:29])[CH2:13][CH2:14]2)=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1529321-(Bis(4-fluorophenyl)methyl)piperazineHCID 516892Sodium BicarbonateHCID 38309693-(4-Chlorosulfonyl-phenyl)-acrylic acid

Product 1

HCID 86624303HCID 86624303, compoundYield 71.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 1-bis(4-fluorophenyl)methyl piperazine (0.47 g, 1.62 mmol) in dioxane (5 mL) a solution of NaHCO3 (0.27 g, 3.24 mmol) in water (4 mL) and a solution of 3-(4-chlorosulfonyl-phenyl)-acrylic acid (8) (0.40 g, 1.62 mmol) were added and the resultant mixture was stirred at ambient temperature for 20 hours. The reaction mixture was poured into water (50 mL), the pH of the medium was brought to ˜4 with 2 N HCl, and extracted with ethyl acetate. The extract was washed successively with water, brine, and dried (Na2SO4). The solvent was removed and the crude product was crystallized from dioxane to give the title compound (0.58 g, 63%) as a white solid. 1H NMR (DMSO-d6, HMDSO), δ: 2.19-2.50 (4H, m, overlapped with a signal of DMSO); 2.80-3.12 (4H, m); 4.42 (1H, s); 6.78 (1H, d, J=16.0 Hz); 7.11 (4H, t, J=9.0 Hz); 7.41 (4H, dd, J=8.6 and 5.6 Hz); 7.72 (1H, d, J=116.0 Hz); 7.78 (2H, d, J=8.2 Hz); 8.00 (2H, d, J=8.2 Hz); 12.68 (1H, br s).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed successively with water, brine
  3. dry with materialdried (Na2SO4)
  4. customThe solvent was removed
  5. customthe crude product was crystallized from dioxane

Sources & evidence

ORD record
ord-9a0d73031c5a4353bdf8da173dab131b
Source dataset
uspto-grants-2011_07
Patent number
US07981895B2

Reaction notes

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