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2-Furancarboxylic acid → 1-(Furan-2-carbonyl)piperidin-4-one

HRID 1642220
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HRID 1642220 반응식
O.Cl.[NH:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.CC[NH+](CC)CC.CC[NH+](CC)CC.C([O-])([O-])=O.[O:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[C:33](O)=[O:34].Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.O.C(#N)C.CO>[O:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[C:33]([N:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1)=[O:34]
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참가 물질

9

반응물 4

HCID 69192-Furancarboxylic acidHCID 2723901PiperonylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 15264167Carbonic acid--N,N-diethylethanamine (1/2)

생성물 1

HCID 208851131-(Furan-2-carbonyl)piperidin-4-one

시약·촉매·용매 4

HCID 887
Methanol
용매
HCID 962Water용매2회
HCID 6342Acetonitrile용매
HCID 6344Dichloromethane용매2회

실험 절차

4-piperidone hydrochloride monohydrate (0.23 g, 1.48 mmol) was dissolved in DCM (5 ml), and to this was added MP-Carbonate resin (0.58 g). This was stirred at room temperature for 2 h. Separately, 2-furoic acid (0.2 g, 1.78 mmol), N N-4-dimethylaminopyridine (cat.), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.85 g, 4.44 mmol) and TEA (0.15 ml) were dissolved in DCM (5 ml) and stirred at room temperature for 2 h. The 2 reaction mixtures were then combined and stirred at room temperature for 18 h. The resulting solution was then filtered and washed with HCl (1M), NaHCO3 then brine. The organic layers were combined and dried over MgSO4 and evaporated to dryness, to yield a yellow oil. 250 mg, (86%), LCMS tr=1.99 min (50% MeOH and 50% water at 0.5 ml/min), m/z M+H 194.16, HPLC tr=1.85 min (Isocratic 90% acetonitrile and 10% water at 1.0 ml/min), 97.09%, 1HNMR (CDCl3, 270 MHz) δ 2.53 (4H, t, J=6.5 Hz, CH2), 4.02 (4H, m, CH2), 9.49 (1H, q, J=1.7 Hz, ArH), 7.07 (1H, dd, J=0.7, 3.5 Hz, ArH), 7.48 (1H, q, J=1.0 Hz, ArH).

후처리

  1. stirringstirred at room temperature for 2 h
  2. customThe 2 reaction mixtures
  3. stirringstirred at room temperature for 18 h
  4. filtrationThe resulting solution was then filtered
  5. washwashed with HCl (1M), NaHCO3
  6. dry with materialdried over MgSO4
  7. customevaporated to dryness
  8. customto yield a yellow oil

출처 및 근거

ORD 기록
ord-4f767e665f984b83b3ad4463de6c35ef
출처 데이터셋
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08119627B2

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