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

HRID 1642220
ノート
印刷プレビュー

反応式

HRID 1642220 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 887
Methanol
溶媒
HCID 962Water溶媒2 回
HCID 6342Acetonitrile溶媒
HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4f767e665f984b83b3ad4463de6c35ef
出典データセット
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08119627B2

反応ノート

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