Dimethylformamide → 2-(3,4-Dichlorophenyl)-1-{4-[(2-Piperidyl)Ethoxy]Benzyl}-1,2,3,4-Tetrahydroisoquinolin-6-Ol

HRID 1358019Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1358019
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:19]CC4C=CC=CC=4)[CH:15]=3)[CH:10]2[CH2:27][C:28]2[CH:33]=[CH:32][C:31](O)=[CH:30][CH:29]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[C:35](=[O:38])([O-])[O-].[K+].[K+].Cl.ClCC[N:45]1[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]1.[CH3:51]N(C=O)C>>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([OH:19])[CH:15]=3)[CH:10]2[CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:38][CH2:35][CH2:51][CH:50]3[CH2:49][CH2:48][CH2:47][CH2:46][NH:45]3)=[CH:30][CH:29]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 234407442-(3,4-Dichlorophenyl)-1-(4-hydroxybenzyl)-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinoline

Produkt 1

HCID 693128582-(3,4-Dichlorophenyl)-1-{4-[(2-Piperidyl)Ethoxy]Benzyl}-1,2,3,4-Tetrahydroisoquinolin-6-OlAusbeute 70 %

Versuchsvorschrift

To a solution of 2-(3,4-dichlorophenyl)-1-(4-hydroxybenzyl)-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinoline (0.5 g, 0.001 mol) in DMF (3 ml) was added potassium carbonate (0.2 g, 0.0015 mol). The reaction was allowed to stir for twenty minutes. To the flask was added 1-(2-chloroethyl)piperidine monohyrdochloride (0.22 g, 0.0012 mol) The reaction was allowed to stir at 80° C. overnight. Solvent was removed. The reaction was diluted with ethyl acetate and water. The aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with brine, dried over MgSO4, filtered and concentrated to yield the title compound (0.42 g, 70% yield): ES-MS (m/z) 601 [M+H]+.

Aufarbeitung

  1. stirringto stir at 80° C. overnight
  2. customSolvent was removed
  3. additionThe reaction was diluted with ethyl acetate and water
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e33be4ee84244e0eb9dfae6d33d3ecb3
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06593322B1

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