Hydrochloric Acid → 4-(3,4-dihydro-6,7-dimethoxy-1-methyl-1H-2-benzopyran-1-yl)piperidine

HRID 275397

Reaktionsgleichung

Reaktionsgleichung von HRID 275397
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][OH:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[NH:14]1[CH2:19][CH2:18][CH:17]([C:20](=O)[CH3:21])[CH2:16][CH2:15]1.Cl>C(O)C>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]2[C:20]([CH:17]3[CH2:18][CH2:19][NH:14][CH2:15][CH2:16]3)([CH3:21])[O:13][CH2:12][CH2:11][C:5]=2[CH:4]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 819113,4-Dimethoxyphenethyl alcoholHCID 27237641-(Piperidin-4-yl)ethan-1-one

Produkt 1

HCID 200879464-(3,4-dihydro-6,7-dimethoxy-1-methyl-1H-2-benzopyran-1-yl)piperidineAusbeute 86,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 200 g of 3,4-dimethoxybenzeneethanol and 163.7 g of 1-(4-piperidinyl)ethanone in 800 ml of ethanol saturated with anhydrous hydrochloric acid was stirred for 15 h at ambient temperature. The mixture was concentrated under vacuum, and the concentrate was diluted with 500 ml of ethanol after which the hydrochloride precipitated. After filtration the hydrochloride was dissolved in water and sodium hydroxide until the pH was 12. The base was extracted with dichloromethane, and the organic phase was washed with water, dried and evaporated to yield 251 g (86.5%) of crude 4-(3,4-dihydro-6,7-dimethoxy-1-methyl-1H-2-benzopyran-1-yl)piperidine.

Aufarbeitung

  1. concentrationThe mixture was concentrated under vacuum
  2. additionthe concentrate was diluted with 500 ml of ethanol after which the hydrochloride
  3. customprecipitated
  4. filtrationAfter filtration the hydrochloride
  5. dissolutionwas dissolved in water
  6. extractionThe base was extracted with dichloromethane
  7. washthe organic phase was washed with water
  8. customdried
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-23dfc06720c841b1a7f789db27249f50
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05393759

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