4-Piperidino-2-naphthol → 3,3-dianisyl-6-piperidino-3H-naphtho[2,1-b]pyran

HRID 54599

Reaktionsgleichung

Reaktionsgleichung von HRID 54599
[N:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]([OH:17])[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:18]([C:27]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=1)(O)[C:28]#[CH:29])[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[CH2:18]([C:27]1([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)[O:17][C:9]2[CH:8]=[C:7]([N:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[C:16]3[C:11]([C:10]=2[CH:29]=[CH:28]1)=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:19]1[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=1

Komponenten

4

Edukt 2

HCID 199595274-Piperidino-2-naphtholHCID 570825081,1-Dianisylprop-2-yn-1-ol

Produkt 1

HCID 677080963,3-dianisyl-6-piperidino-3H-naphtho[2,1-b]pyran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

1-Chloro-4-piperidino-2-naphthol (3.0 g;0.0115 mol), prepared as in 1(a) above, dissolved in 1.25M aqueous NaOH (100 ml) was stirred and heated to 75°-80° C. To the solution was added (50/50) Raney Nickel (14.0 g) portionwise over 1 hour. The mixture was stirred for 1.5 h, cooled then filtered through celite with washing (3×2M NaOH). The filtrate was neutralised with conc. HCl and extracted into CH2Cl2, dried and evaporated to yield crude 4-piperidino-2-naphthol (1.46 g;56%) as a red-orange oil. Purification by flash chromatography over silica (CH2Cl2) gave 4-piperidino-2-naphthol (of structure 4a below) as a red oil. ##STR16## (c) A mixture of 4-piperidino-2-naphthol (1.00 g; 0.0044 mol) , prepared as described in 1(b) above, 1,1-dianisylprop-2-yn-1-ol(1.18 g;0.0044 mol), acidic alumina Brockmann 1 (4 g) and toluene (40.0 ml) was heated and stirred for 1.5 h, cooled and filtered. The filtrate was washed with 2M NaOH then water, dried and evaporated to give a red gum. Purification of the gum by flash chromatography over silica (20% ethylacetate in hexane) affored an orange gum which upon trituration with pet. ether (40-60)/diethyl ether yielded 3,3-dianisyl-6-piperidino -3H-naphtho[2,1-b]pyran (of structure 5a below) as an off-white solid (5% yield), m.pt. 114°-119° C. ##STR17##

Aufarbeitung

  1. customprepared
  2. temperaturecooled
  3. filtrationfiltered
  4. washThe filtrate was washed with 2M NaOH
  5. dry with materialwater, dried
  6. customevaporated
  7. customto give a red gum
  8. customPurification of the gum by flash chromatography over silica (20% ethylacetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-f64781a8c6524d229c035e67a321aaf7
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05623005

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