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

HRID 2380963노트

반응식

HRID 2380963 반응식
[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

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-bb7d438a239e449da2f7f671a3b72c73
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08258138B2

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