Potassium Carbonate → 2-[3-(4-Methoxy-1-piperidinyl)propyl]-1H-isoindole-1,3(2H)-dione

HRID 1669215

Reaktionsgleichung

Reaktionsgleichung von HRID 1669215
[CH3:1][O:2][CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.Br[CH2:10][CH2:11][CH2:12][N:13]1[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:23].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][O:2][CH:3]1[CH2:8][CH2:7][N:6]([CH2:10][CH2:11][CH2:12][N:13]2[C:17](=[O:18])[C:16]3[C:15](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:14]2=[O:23])[CH2:5][CH2:4]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 21611N-3-BromopropylphthalimideHCID 776664-Methoxypiperidine

Produkt 1

HCID 574476972-[3-(4-Methoxy-1-piperidinyl)propyl]-1H-isoindole-1,3(2H)-dioneAusbeute 59,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A suspension of 4-methoxypiperidine (286) (4.1 g, 35.3 mmol), N-(3-bromopropyl)phthalimide (9.0 g, 33.6 mmol) and K2CO3 (7.0 g, 50.4 mmol) in DMF (80 mL) was stirred at 50° C. for 16 h. The solution was cooled, the solvent evaporated and the residue partitioned between water (150 mL) and EtOAc (150 mL). The organic fraction was washed with water (2×50 mL) and brine (50 mL), dried and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (0-5%) of MeOH/DCM, to give phthalimide 305 (6.0 g, 59%) as a white solid: 1H NMR δ 7.81-7.86 (m, 2H, Harom), 7.67-7.73 (m, 2H, Harom), 3.75-3.79 (t, J=7.0 Hz, 2H, CH2N), 3.28 (s, 3H, OCH3), 3.09-3.17 (m, 1H, CHO), 2.63-2.70 (m, 2H, CH2N), 2.39 (t, J=7.0 Hz, 2H, CH2N), 2.01-2.08 (m, 2H, CH2N), 1.85 (p, J=7.0 Hz, 2H, CH2), 1.74-1.81 (m, 2H, CH2), 1.37-1.46 (m, 2H, CH2). Anal. calcd for C17H22N2O3: C, 67.5; H, 7.3; N, 9.3. Found: C, 67.3; H, 7.4; N, 9.3%.

Aufarbeitung

  1. temperatureThe solution was cooled
  2. customthe solvent evaporated
  3. customthe residue partitioned between water (150 mL) and EtOAc (150 mL)
  4. washThe organic fraction was washed with water (2×50 mL) and brine (50 mL)
  5. customdried
  6. customthe solvent evaporated
  7. customThe residue was purified by chromatography
  8. washeluting with a gradient (0-5%) of MeOH/DCM

Quellen und Nachweise

ORD-Eintrag
ord-9b7b960dd3fe4fb9a99f863ec5ee8752
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989451B2

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