Sodium hydride → 5-(3-(tetrahydropyran-2-yloxy)-1propyl)-10,11dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonitrile

HRID 234677Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 234677
[H-].[Na+].[CH:3]1[C:13]2[CH2:12][CH2:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[CH:8]([C:18]#[N:19])[C:7]=2[CH:6]=[CH:5][CH:4]=1.[O:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]1[O:26][CH2:27][CH2:28][CH2:29]Br>C1(C)C=CC=CC=1>[O:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]1[O:26][CH2:27][CH2:28][CH2:29][C:8]1([C:18]#[N:19])[C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[CH2:11][CH2:12][C:13]2[CH:3]=[CH:4][CH:5]=[CH:6][C:7]1=2

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyranHCID 1409111110,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonitrile

Produkt 1

HCID 187993365-(3-(tetrahydropyran-2-yloxy)-1propyl)-10,11dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonitrileAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel3×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

In a 50 ml roundbottom flask equipped with magnetical stirring, thermometer and addition funnel, sodium hydride (0.8 g, 0.02 mol, 60% dispersion in oil) was suspended in dry toluene under an atmosphere of nitrogen. A solution of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonitrile (3.0 g, 0.014 mol, prepared in a similar way as described in J. Med. Chem., 6, (1963), 251) in dry toluene (15 ml) was added. The reaction mixture was heated to reflux temperature in 30 minutes and then heated at reflux temperature for 150 minutes. After cooling to about 50° C., a solution of 3-bromopropyl tetrahydropyranyl ether (4.5 g, 0.02 mol) in dry toluene (6 ml) was added dropwise. The reaction mixture was heated at reflux temperature for 5 h and then left stirring at room temperature overnight. After filtration of precipitated salts, the solution was washed with 1N HCl (100 ml), diluted with more toluene (100 ml) and finally washed with water. After drying (MgSO4), the organic phase was evaporated in vacuo affording 7.2 g (99%) of 5-(3-(tetrahydropyran-2-yloxy)-1-propyl)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonitrile.

Aufarbeitung

  1. customIn a 50 ml roundbottom flask equipped with magnetical stirring
  2. additionthermometer and addition funnel
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux temperature in 30 minutes
  5. temperatureheated
  6. temperatureat reflux temperature for 150 minutes
  7. temperatureThe reaction mixture was heated
  8. temperatureat reflux temperature for 5 h
  9. waitleft
  10. filtrationAfter filtration of precipitated salts
  11. washthe solution was washed with 1N HCl (100 ml)
  12. additiondiluted with more toluene (100 ml)
  13. washfinally washed with water
  14. dry with materialAfter drying (MgSO4)
  15. customthe organic phase was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-dfa4422c36df4c33bc32416ad3ac3d34
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05595989

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