1,2,3,4-Tetrahydroisoquinoline → 1-(3-bromophenoxy)-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol

HRID 1399815Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1399815
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[O:5][CH2:6][CH:7]1[CH2:9][O:8]1.[CH2:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][NH:14]1.CC(=O)OCC>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[O:5][CH2:6][CH:7]([OH:8])[CH2:9][N:14]1[CH2:15][CH2:16][C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:13]1

Komponenten

5

Edukt 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 8857Ethyl AcetateHCID 38653422-[(3-Bromophenoxy)methyl]oxirane

Produkt 1

HCID 429098461-(3-bromophenoxy)-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-olAusbeute 78,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 2-((3-bromophenoxy)methyl)oxirane (1.5 g, 6.55 mmol) in MeOH (15 mL) were added 1,2,3,4-tetrahydroisoquinoline (1.0 g, 7.86 mmol) at 8° C. The mixture was refluxed for 16 h. TLC (PE:EA=2:1) showed that the reaction was completed and the mixture was concentrated to yield crude material which was purified using column chromatography on silica gel to give the desired compound (1.8 g, 78.3%) as colorless oil. LCMS (m/z): 362.1/363.1 [M+H]+/[M+2H]+

Aufarbeitung

  1. temperatureThe mixture was refluxed for 16 h
  2. concentrationthe mixture was concentrated
  3. customto yield crude material which
  4. customwas purified

Quellen und Nachweise

ORD-Eintrag
ord-018d08d3331144a586ebf6636445948f
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906900B2

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