Phenethylamine → HCID 89837825, Verbindung

HRID 1050738Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1050738
CC(C(N)=O)[C:3]1[C:8]([C:9]([OH:11])=O)=[CH:7][C:6]([F:12])=[C:5]([Cl:13])[CH:4]=1.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1.[CH2:39]([NH2:47])[CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.[N:48]1C=C[CH:51]=[CH:50][CH:49]=1>C(OCC)(=O)C>[Cl:13][C:5]1[CH:4]=[C:3]2[C:8]([C:9](=[O:11])[N:47]([CH2:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:49]([CH2:50][CH3:51])=[N:48]2)=[CH:7][C:6]=1[F:12]

Komponenten

6

Edukt 4

HCID 1001PhenethylamineHCID 1049PyridineHCID 7540Triphenyl phosphiteHCID 89837476HCID 89837476, Verbindung

Produkt 1

HCID 89837825HCID 89837825, VerbindungAusbeute 27,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The crude solid (3 g) from step 3 above mixed with triphenyl phosphite (4 mL, 14.81 mmol) in pyridine (15 mL) was stirred at rt for 4 h. The mixture was added with phenethylamine (1.55 mL, 12.18 mmol), irradiated with microwave 250 W to refluxing for 15 min. The mixture was diluted with ethyl acetate (50 mL), washed with water (2×50 mL). The ethyl acetated solution was mixed with water (50 mL) and kept at rt to give solid form. The solution was filtered to give yellow solid title compound (1.1 g, 27.2%). mp=150-152° C. (recrystallized from ethyl acetate); 1H NMR (400 MHz, DMSO-d6) δ 1.19 (t, J=7.2 Hz, 3H, CH3), 2.76 (q, J=7.2 Hz, 2H, CH2), 2.93 (br t, J=7.6 Hz, 2H, CH2), 4.19 (br t, J=7.6 Hz, 2H, CH2), 7.20-7.31 (m, 5H, ArH), 7.80 (d, J=6.4 Hz, 1H, ArH), 7.91 (d, J=8.8 Hz, 1H, ArH), 13C NMR (100 MHz, DMSO-d6) δ 10.6, 26.9, 33.5, 44.8, 112.2, 112.4, 119.8, 119.9, 126.6, 126.8, 127.0, 128.5, 128.7, 128.8, 138.0, 144.1, 153.6, 156.1, 158.9, 160.0; Anal. (C18H16ClFN2O) C, H, N. Calcd: 65.36, 4.88, 8.47. Found: 65.09, 4.77, 8.50.

Aufarbeitung

  1. customirradiated with microwave 250 W
  2. temperatureto refluxing for 15 min
  3. washwashed with water (2×50 mL)
  4. additionThe ethyl acetated solution was mixed with water (50 mL)
  5. customkept at rt
  6. customto give solid form
  7. filtrationThe solution was filtered

Quellen und Nachweise

ORD-Eintrag
ord-2ea9c1c789f047f29e2af3a2455dd4da
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09387209B2

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