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Hydrochloric Acid → HCID 20079710, Verbindung

HRID 1464145
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1464145
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[S:16][CH2:15][CH2:14][CH2:13][S:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C([Li])CCC.[Cl:22][CH2:23][CH2:24][CH2:25][N:26]([CH3:44])[CH2:27][C:28]1([C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[C:36]([O:42][CH3:43])[CH:35]=2)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.Cl>CCCCCC.O1CCOCC1.O1CCCC1>[ClH:22].[CH3:43][O:42][C:36]1[CH:35]=[C:34]([C:28]2([CH2:27][N:26]([CH3:44])[CH2:25][CH2:24][CH2:23][C:11]3([C:5]4[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=4)[S:12][CH2:13][CH2:14][CH2:15][S:16]3)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]2)[CH:39]=[CH:38][C:37]=1[O:40][CH3:41]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 110105922-(3,4-Dimethoxyphenyl)-1,3-dithianeHCID 20079736HCID 20079736, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 20079710HCID 20079710, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×
HCID 8058HexaneLösungsmittel
HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

A solution of 2.56 g (0.01 mol) of 2-(3,4-dimethoxyphenyl)-m-dithiane in 20 ml of abs. tetrahydrofuran was cooled to -60° in a sulphonation flask while gassing with dry argon and treated dropwise within 15 minutes with 4.68 ml (0.0075 mol) of a solution of butyllithium in hexane, whereby the temperature was held at -60°. Thereafter, the solution was stirred at -20° for 2 hours, then again cooled to -60° and treated dropwise with a solution of 1.70 g (0.005 mol) of N-(3-chloropropyl)-1-(3,4-dimethoxyphenyl)-N-methylcyclohexanemethanamine in 20 ml of abs. tetrahydrofuran. After 16 hours at -20° and 4 hours at room temperature the solution was poured on to ice-water and the mixture was washed three times with ether. The ethereal extracts were dried over magnesium sulphate, filtered and evaporated under reduced pressure. The residual oil was chromatographed on silica gel 60 with toluene/ethyl acetate (8:2 ). After evaporation of the solvent there was obtained a colourless oil which was dissolved in a small amount of abs. dioxan and treated with an excess of hydrogen chloride in abs. dioxan, whereby N-[[1-(3,4-dimethoxyphenyl)cyclohexyl]methyl]-2-(3,4-dimethoxyphenyl)-N-methyl-m-dithiane-2-propanamine hydrochloride was obtained as a solid white foam.

Aufarbeitung

  1. customwas held at -60°
  2. temperatureagain cooled to -60°
  3. waitAfter 16 hours at -20°
  4. washthe mixture was washed three times with ether
  5. dry with materialThe ethereal extracts were dried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residual oil was chromatographed on silica gel 60 with toluene/ethyl acetate (8:2 )
  9. customAfter evaporation of the solvent there
  10. customwas obtained a colourless oil which
  11. dissolutionwas dissolved in a small amount of abs

Quellen und Nachweise

ORD-Eintrag
ord-52e9aa0a278d4b0685ebf8aa61681b7f
Quelldatensatz
uspto-grants-1994_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05302727

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