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

HRID 1642220Notes

Reaction equation

HRID 1642220 reaction equation
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]

Participants

9

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-4f767e665f984b83b3ad4463de6c35ef
Source dataset
uspto-grants-2012_02
Patent number
US08119627B2

Reaction notes

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