4-Aminobenzoic Acid → (4-Aminophenyl)(4-phenylpiperazin-1-yl)methanone

HRID 2380963Notes

Reaction equation

HRID 2380963 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.Cl.C(N=C=NCCCN(C)C)C.O.OC1C2N=NNC=2C=CC=1.[C:34]1([N:40]2[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(N(CC)CC)C>C(#N)C.O>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:43]2[CH2:44][CH2:45][N:40]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:41][CH2:42]2)=[O:8])=[CH:9][CH:10]=1

Participants

8

Reactant 5

HCID 9784-Aminobenzoic AcidHCID 70961-PhenylpiperazineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178526939HCID 178526939, compound

Product 1

HCID 12932882(4-Aminophenyl)(4-phenylpiperazin-1-yl)methanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of 4-aminobenzoic acid (5 g, 36.5 mmol) in acetonitrile (100 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (7.67 g, 40.2 mmol), hydroxybenzotriazole hydrate (0.49 g, 3.65 mmol), 1-phenylpiperazine (11.2 ml, 3.65 mmol) followed by triethylamine (12.8 ml, 91.3 mmol) and the reaction mixture was stirred at room temperature for 16 hours. The reaction was diluted with the addition of water and the resulting aqueous mixture extracted using dichloromethane (3×100 ml). The organics were combined, dried over magnesium sulfate and concentrated in vacuo. The resulting residue was purified by flash column chromatography (SiO2) eluting with ethylacetate/dichloromethane (1:1) to afford the title compound as an off white solid. HPLC retention time 7.1 min. Mass spectrum (ES+) m/z 282 (M+H).

Workup

  1. extractionthe resulting aqueous mixture extracted
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was purified by flash column chromatography (SiO2)
  5. washeluting with ethylacetate/dichloromethane (1:1)

Sources & evidence

ORD record
ord-bb7d438a239e449da2f7f671a3b72c73
Source dataset
uspto-grants-2012_09
Patent number
US08258138B2

Reaction notes

Loading…