Benzylamine → Benzyl-(3-methoxy-4-nitro-benzyl)amine

HRID 1821795Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1821795
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[CH2:6]Br.C(N(CC)CC)C.[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[CH2:21]([NH:28][CH2:6][C:5]1[CH:8]=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

5

Edukt 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 126216043-Methoxy-4-nitrobenzyl bromide

Produkt 1

HCID 22046378Benzyl-(3-methoxy-4-nitro-benzyl)amineAusbeute 73,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a 150 mL round bottomed flask containing 1.97 g (8.0 mmol) of 3-methoxy-4-nitro-benzyl bromide in 20 mL THF was added, 2.4 g (24 mmol, 3 eq.) of triethylamine followed by 2.5 g (24 mmol, 3 eq.) of benzylamine. The mixture was stirred at room temperature for 2 h, and was then partitioned between 50 mL ethyl acetate and brine. The organic phase was dried over MgSO4 and concentrated. The residue was purified by flash chromatography, eluting with 14% MeOH in dichloromethane to give 1.6 g (73%) of the benzyl amine as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 7.84 (d, J=8.61 Hz, 1H), 7.34 (m, 5H), 7.16 (s, 1H), 6.99 (d, J=8.61 Hz, 1H), 3.97 (s, 3H), 3.86 (s, 2H), 3.81 (s, 2H).

Aufarbeitung

  1. additionwas added
  2. customwas then partitioned between 50 mL ethyl acetate and brine
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. washeluting with 14% MeOH in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-663cbb0157e547ae98bd86dd638b58f0
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07608618B2

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