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

HRID 1051461Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1051461
[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>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

4

Edukt 2

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

Produkt 1

HCID 429098461-(3-bromophenoxy)-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol

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) was added 1,2,3,4-tetrahydroisoquinoline (1.0 g, 7.86 mmol) at 20° C. The mixture was heated at reflux temperature for 16 h, until the reaction was shown to be complete. The mixture then was concentrated to provide the crude which was purified using column chromatography on silica gel producing the desired 1-(3-bromophenoxy)-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol (1.8 g, 78.3%) as colorless oil. LCMS (m/z): 362.1 (M+1).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 16 h
  3. concentrationThe mixture then was concentrated
  4. customto provide the crude which
  5. customwas purified

Quellen und Nachweise

ORD-Eintrag
ord-0e5aeb7a74724ab6b38efcdf1b765aaa
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09388173B2

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