Piperidine → 2-(4-Fluorophenyl)-1-{4-[(2-piperidyl)ethoxy]benzoyl}-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinoline

HRID 1180194Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1180194
Br[CH2:2][CH2:3][O:4][C:5]1[CH:37]=[CH:36][C:8]([C:9]([CH:11]2[C:20]3[C:15](=[CH:16][C:17]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:18][CH:19]=3)[CH2:14][CH2:13][N:12]2[C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)=[O:10])=[CH:7][CH:6]=1.[NH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1>CN(C)C=O>[F:35][C:32]1[CH:31]=[CH:30][C:29]([N:12]2[CH2:13][CH2:14][C:15]3[C:20](=[CH:19][CH:18]=[C:17]([O:21][CH2:22][C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH:16]=3)[CH:11]2[C:9](=[O:10])[C:8]2[CH:36]=[CH:37][C:5]([O:4][CH2:3][CH2:2][CH:39]3[CH2:40][CH2:41][CH2:42][CH2:43][NH:38]3)=[CH:6][CH:7]=2)=[CH:34][CH:33]=1

Komponenten

4

Edukt 2

HCID 8082PiperidineHCID 234408451-[4-(2-Bromethoxy)benzoyl]-2-(4-fluorophenyl)-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinoline

Produkt 1

HCID 536534802-(4-Fluorophenyl)-1-{4-[(2-piperidyl)ethoxy]benzoyl}-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinolineAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 1-[4-(2-bromethoxy)benzoyl]-2-(4-fluorophenyl)-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinoline (0.80 g, 1.43 mmol) and piperidine (0.86 g, 10.1 mmol) in dimethylformamide was stirred at room temperature for 3 hours. The reaction was quenched with brine and extracted with ethyl acetate. The organic layer was dried over MgSO4, filtered, concentrated, and purified by chromatography (SiO2, ethyl acetate and 3-5% methanol/ethyl acetate) to provide the title compound (0.594 g, 74% yield): 1H NMR (CDCl3) 8.00 (m, 2H), 7.40 (m, 4H), 6.79-6.92 (m, 10H), 5.87 (s, 1H), 5.02 (s, 2H), 4.15 (t, 2H), 3.72 (m, 1H), 3.48 (m, 1H), 3.07 (m, 1H), 2.79 (t and m, 3H), 2.51 (m, 4H), 1.61 (m, 4H), 1.46 (m, 2H); ES-MS (m/z) 565 [M+H]+.

Aufarbeitung

  1. customThe reaction was quenched with brine
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by chromatography (SiO2, ethyl acetate and 3-5% methanol/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-c4671de1b13c4b778b3671a39417e749
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07279489B2

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