Sodium Hydroxide → 1-(Benzyloxy)but-3-en-2-amine hydrochloride

HRID 595327Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 595327
[CH2:1]([O:8][CH2:9][CH:10]([NH:13]C(=O)C(Cl)(Cl)[Cl:16])[CH:11]=[CH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O>[ClH:16].[CH2:1]([O:8][CH2:9][CH:10]([NH2:13])[CH:11]=[CH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 13416079N-[1-(Benzyloxy)but-3-en-2-yl]-2,2,2-trichloroacetamide

Produkt 1

HCID 135179031-(Benzyloxy)but-3-en-2-amine hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of N-[1-(benzyloxy)but-3-en-2-yl]-2,2,2-trichloroacetamide (7.5 g, 23 mmol) and sodium hydroxide (4.0 M in H2O, 40 mL, 160 mmol) was stirred and heated to 80° C. for 5 hours. The reaction mixture was cooled to ambient temperature, diluted with water, and extracted with ethyl acetate. The organic layer was separated and extracted with hydrochloric acid (2N). The aqueous layer was concentrated under reduced pressure to afford 1-(benzyloxy)but-3-en-2-amine hydrochloride. MS ESI calc'd. for C11H16NO [M+H]+ 178. found 178. 1H NMR (400 MHz, DMSO-d6) δ 8.38 (s, 2H), 7.37-7.28 (m, 5H), 5.89-5.80 (m, 1H), 5.44-5.32 (m, 2H), 4.57-4.50 (m, 2H), 3.99 (s, 1H), 3.62-3.55 (m, 2H).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. extractionextracted with hydrochloric acid (2N)
  5. concentrationThe aqueous layer was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-cfa7854ff5cf46228c219b7efc94e6d1
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242984B2

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