Water → (4-Benzyl-1,4-oxazepan-2-ylmethyl)-phenyl amine

HRID 988782Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 988782
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].[I-].[CH2:10]([N:17]1[CH2:23][CH2:22][CH2:21][O:20][CH:19]([CH2:24]Cl)[CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>C(O)CCC.C(Cl)Cl>[CH2:10]([N:17]1[CH2:23][CH2:22][CH2:21][O:20][CH:19]([CH2:24][NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:18]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 5238Sodium IodideHCID 6115AnilineHCID 103993654-Benzyl-2-(chloromethyl)-1,4-oxazepane

Produkt 1

HCID 21904409(4-Benzyl-1,4-oxazepan-2-ylmethyl)-phenyl amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2631-ButanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Aniline (2.59 mL, 28.4 mmol) and NaI (4.06 g, 27.1 mmol) were added to a solution of 4-benzyl-2-chloromethyl-1,4-oxazepane (79) (6.49 g, 27.1 mmol) in n-butanol (68 mL, 0.4 M), and the reaction was heated to 110° C. until the reaction was judged complete by TLC (4 h). The reaction was cooled to room temperature, and water and CH2Cl2 were added. The organic layer was removed, and the aqueous layer was extracted with CH2Cl2 (2×). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to achieve (4-benzyl-1,4-oxazepan-2-ylmethyl)-phenyl amine 80, which was used without purification in the next reaction. 1H NMR (partial, CDCl3) 4.08-3.86 (3H, m), 3.80 (1H, d, J=13.3 Hz), 3.73 (1H, d, J=13.3 Hz), 3.22-3.05 (2H, m), 2.95-2.70 (3H, m), 2.64 (1H, dd, J=13.6, 7.6 Hz), 2.1-1.9 (2H, m) ppm. 13C NMR (CDCl3) 148.33, 139.38, 129.28, 129.11, 128.46, 127.23, 117.44, 113.13, 76.70, 67.49, 62.92, 59.35, 54.76, 46.93, 30.75 ppm. LRMS: 296.68.

Aufarbeitung

  1. customwas judged complete by TLC (4 h)
  2. temperatureThe reaction was cooled to room temperature
  3. customThe organic layer was removed
  4. extractionthe aqueous layer was extracted with CH2Cl2 (2×)
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customwas used without purification in the next reaction

Quellen und Nachweise

ORD-Eintrag
ord-8482a8fc13ff4a59aaaa9fa049514079
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06635661B2

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