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

HRID 2114746Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2114746
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-ed76d369766a436f9bd0ce6713ead0f0
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07435729B2

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