Hydrochloric Acid → 1-(7,8-Dimethoxy-1,2-dihydro-4-naphthoyl)-4-(3,4,5-trimethoxybenzyl)piperazine hydrochloride

HRID 1638776

Reaktionsgleichung

Reaktionsgleichung von HRID 1638776
P(C#N)(=O)(OCC)OCC.[CH3:11][O:12][C:13]1[C:22]([O:23][CH3:24])=[C:21]2[C:16]([C:17]([C:25]([OH:27])=O)=[CH:18][CH2:19][CH2:20]2)=[CH:15][CH:14]=1.[ClH:28].Cl.[CH3:30][O:31][C:32]1[CH:33]=[C:34]([CH:42]=[C:43]([O:47][CH3:48])[C:44]=1[O:45][CH3:46])[CH2:35][N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1.Cl>C(OCC)C.O.CN(C)C=O.C(N(CC)CC)C>[ClH:28].[CH3:11][O:12][C:13]1[C:22]([O:23][CH3:24])=[C:21]2[C:16]([C:17]([C:25]([N:39]3[CH2:38][CH2:37][N:36]([CH2:35][C:34]4[CH:42]=[C:43]([O:47][CH3:48])[C:44]([O:45][CH3:46])=[C:32]([O:31][CH3:30])[CH:33]=4)[CH2:41][CH2:40]3)=[O:27])=[CH:18][CH2:19][CH2:20]2)=[CH:15][CH:14]=1

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 76257Diethyl cyanophosphonateHCID 128285011-[(3,4,5-Trimethoxyphenyl)methyl]piperazine;dihydrochlorideHCID 198412007,8-Dimethoxy-1,2-dihydro-4-naphthoic acid

Produkt 1

HCID 198412141-(7,8-Dimethoxy-1,2-dihydro-4-naphthoyl)-4-(3,4,5-trimethoxybenzyl)piperazine hydrochlorideAusbeute 67,7 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Diethyl phosphorocyanidate (1.2 ml) is added dropwise to a mixture of 7,8-dimethoxy-1,2-dihydro-4-naphthoic acid (0.5 g), 1-(3,4,5-trimethoxybenzyl)piperazine dihydrochloride (0.87 g), triethylamine (0.86 g) and N,N-dimethylformamide (20 ml) with stirring. After stirring for one hour at room temperature, water (100 ml) is added to the reaction mixture and the mixture is extracted with ethyl acetate (100 ml). The organic layer is washed with water, dried and concentrated under reduced pressure. The resulting oily substance is purified by silica gel column chromatography (hexane: acetone=1:1). The product thus obtained is dissolved in ethyl ether and the solution is treated with 5N ethanolic hydrogen chloride (2 ml) to give 1-(7,8-dimethoxy-1,2-dihydro-4-naphthoyl)-4-(3,4,5-trimethoxybenzyl)piperazine hydrochloride (0.75 g) as colorless powder.

Aufarbeitung

  1. stirringAfter stirring for one hour at room temperature
  2. extractionthe mixture is extracted with ethyl acetate (100 ml)
  3. washThe organic layer is washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting oily substance is purified by silica gel column chromatography (hexane: acetone=1:1)
  7. customThe product thus obtained

Quellen und Nachweise

ORD-Eintrag
ord-12d07bc7a4e142be87bcf8115211c9f3
Quelldatensatz
uspto-grants-1989_11
Patentnummer
US04880809

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