Trifluoroacetic acid → 1-[4-(2-Bromethoxy)benzoyl]-2-(4-fluorophenyl)-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinoline

HRID 2114745Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2114745
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:12]=2)=[CH:4][CH:3]=1.[Br:25][CH2:26][CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]([CH:37]=O)=[O:36])=[CH:31][CH:30]=1.FC(F)(F)C(O)=O>>[Br:25][CH2:26][CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]([CH:37]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH2:18][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)=[CH:14][CH:15]=3)[CH2:10][CH2:9][N:8]2[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[O:36])=[CH:31][CH:30]=1

Komponenten

4

Edukt 3

HCID 6422Trifluoroacetic acidHCID 23440827HCID 23440827, VerbindungHCID 23440828(4-Fluorophenyl){2-[3-(phenylmethoxy)phenyl]ethyl}amine

Produkt 1

HCID 234408451-[4-(2-Bromethoxy)benzoyl]-2-(4-fluorophenyl)-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinolineAusbeute 78,4 %

Versuchsvorschrift

To a solution of (4-fluorophenyl) {2-[3-(phenylmethoxy)phenyl]ethyl}amine (0.643 g, 2.0 mmol) and [4-(2-bromoethoxy)phenyl]glyoxal (0.617 g, 2.4 mmol) was added trifluoroacetic acid (0.342 g, 3.0 mmol). The reaction stirred at room temperature for 4 hours. The reaction was quenched with saturated sodium bicarbonate and extracted with ethyl acetate. The organic layer was dried over MgSO4, filtered, concentrated, and purified by column chromatography (SiO2, 20% ethyl acetate/hexane) to provide the title compound (0.879 g, 78% yield): 1H NMR (CDCl3) 8.00 (d, 2H), 7.40 (m, 4H), 7.18 (m, 1H), 7.07 (d, 1H), 6.79-6.92 (m, 8H), 5.85 (s, 1H), 5.02 (s, 2H), 4.33 (t, 2H), 3.71 (m, 1H), 3.64 (t, 2H), 3.47 (m, 1H), 3.07 (m, 1H), 2.87 (m, 1H); ES-MS (m/z) 560 [M+H]+.

Aufarbeitung

  1. customThe reaction was quenched with saturated sodium bicarbonate
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by column chromatography (SiO2, 20% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-389151764c204cc8bc7145b5b75ba0a9
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07435729B2

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