Acetic Anhydride → 5-Iodo-1-methyl-3,4-dihydroisoquinoline

HRID 532863

Reaktionsgleichung

Reaktionsgleichung von HRID 532863
[I:1][C:2]1[CH:13]=[CH:12][CH:11]=[CH:10][C:3]=1[CH2:4][CH2:5][NH:6][C:7](=O)[CH3:8].IC1C=CC=CC=1CCN.CC(OC(C)=O)=O>O1CCOCC1>[I:1][C:2]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:3]=1[CH2:4][CH2:5][N:6]=[C:7]2[CH3:8]

Komponenten

5

Edukt 3

HCID 7918Acetic AnhydrideHCID 105146162-(2-Iodophenyl)ethanamineHCID 86711313N-(2-iodophenethyl)acetamide

Produkt 1

HCID 867113155-Iodo-1-methyl-3,4-dihydroisoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

N-(2-iodophenethyl)acetamide. A solution of 2-(2-iodophenyl)ethanamine (13.5 g, 54.6 mmol) and Ac2O (10.3 mL, 109 mmol) in 1,4-dioxane (200 mL) was heated to 100° C. for 45 min. The reaction was then allowed to cool to RT and concentrated in vacuo. The resulting residue was taken up in DCM and washed with a saturated aq. solution of NaHCO3— gas formation! The organic phase was separated, dried over Na2SO4, filtered and concentrated in vacuo to give the title compound as a yellow oil (16.2 g) which was used as it is in the next step. UPLC-MS: MS 290.3 (M+H+); UPLC rt 0.96 min.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. washwashed with a saturated aq. solution of NaHCO3— gas formation
  3. customThe organic phase was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ed8a50e664244039ad822f31729a0b9c
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853203B2

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