Sodium Carbonate → 1-Phthalimido-1-(4-methoxyphenyl)propane

HRID 2301938Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2301938
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([NH2:12])[CH2:10][CH3:11])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Na+].[Na+].C(N1[C:28](=[O:29])[C:27]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]2[C:25]1=[O:34])(OCC)=O>O.C(#N)C>[C:25]1(=[O:34])[N:12]([CH:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:10][CH3:11])[C:28](=[O:29])[C:27]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]12

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 31432871-(4-Methoxyphenyl)propan-1-amine

Produkt 1

HCID 120499681-Phthalimido-1-(4-methoxyphenyl)propaneAusbeute 38,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-(4′methoxyphenyl)propylamine (2.5 grams, 15.2 mmol) and sodium carbonate (1.74 grams, 16.4 mmol) in a mixture of water (50 milliliters) and acetonitrile (50 milliliters) was added N-carbethoxyphthalimide (3.34 grams, 15.2 mmol). The resulting suspension was stirred for 4.5 hours at room temperature, the acetonitrile was removed in vacuo and a solid formed. The slurry was filtered and the solid was washed with water and air dried to afford 1.73 grams (39%) of crude product as a white powder. The crude product was recrystallized from hexane/ethyl acetate and dried in vacuo (60° C., <1 mm) to afford 1.71 grams (38%) of the product as white crystals: mp 85-86° C.; 1H NMR (DMSO-d6) δ7.92-7.79(m, 4H), 7.46-7.28(m,2 H), 6.97-6.83(m, 2 H), 5.19-5.06(m, 1 H), 3.72(s, 3H), 2.56-2.13(m, 2 H), 0.87(t, J=7.3 Hz, 3 H);13C NMR (DMSO-d6) δ167.8, 1.5, 134.6, 131.7, 131.0, 128.6, 123.1, 113.7, 55.2, 54.9, 23.8, 11.3. Anal. Calculated for C18H17NO3. Theoretical: C,73.20; H,5.80; N, 4.74. Found: C,73.24; H, 5.74; N, 4.86. HPLC 100%.

Aufarbeitung

  1. customthe acetonitrile was removed in vacuo
  2. customa solid formed
  3. filtrationThe slurry was filtered
  4. washthe solid was washed with water and air
  5. customdried
  6. customto afford 1.73 grams (39%) of crude product as a white powder
  7. customThe crude product was recrystallized from hexane/ethyl acetate
  8. customdried in vacuo (60° C., <1 mm)

Quellen und Nachweise

ORD-Eintrag
ord-bca56d89577540319a8faadb703d4d0b
Quelldatensatz
uspto-grants-2002_08
Patentnummer
US06429221B1

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