Hydrochloric Acid → 4-[4-(2-Methoxy-phenyl)-piperazin-1-yl]-2-phenyl-1(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]oct-6-yl)-butan-1-one

HRID 975819

Reaktionsgleichung

Reaktionsgleichung von HRID 975819
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18](O)=[O:19])[CH2:11][CH2:10]1.[CH3:27][C:28]12[CH2:35][CH:32]([NH:33][CH2:34]1)[CH2:31][C:30]([CH3:37])([CH3:36])[CH2:29]2.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.[OH-].[Na+].Cl>C(Cl)Cl.CCOCC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18]([N:33]2[CH2:34][C:28]3([CH3:27])[CH2:35][CH:32]2[CH2:31][C:30]([CH3:37])([CH3:36])[CH2:29]3)=[O:19])[CH2:13][CH2:14]1

Komponenten

9

Edukt 6

HCID 313Hydrochloric Acid2×HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 1037871,3,3-Trimethyl-6-azabicyclo(3.2.1)octaneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 98634284-[4-(2-Methoxyphenyl)piperazin-1-yl]-2-phenylbutanoic acid

Produkt 1

HCID 199683574-[4-(2-Methoxy-phenyl)-piperazin-1-yl]-2-phenyl-1(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]oct-6-yl)-butan-1-oneAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 4-[4-(2-methoxyphenyl) piperazin-1-yl]-2-phenylbutanoic acid (1.70 g, 5.0 mmole), 1,3,3-trimethyl-6-azabicyclo[3.2.1]-octane (0.77 g, 5.0 mmole), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.96 g, 5.0 mmole) and triethylamine (0.55 g, 5.0 mmole) in methylene chloride (10 mL) was stirred at ambient temperature for 48 hr. The mixture was poured into 1N sodium hydroxide (75 mL) and extracted with ethyl acetate (3×75 mL). The combined ethyl acetate layer was washed with water (100 mL) and brine (100 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum to give crude product. This material was treated with 1.1 equivalent of 1N hydrogen chloride in ether (100 mL) to give 1.15 g of the title compound as the hydrochloride sequihydrate, m.p. 110°-145° C. (dec.).

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×75 mL)
  2. washThe combined ethyl acetate layer was washed with water (100 mL) and brine (100 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customto give crude product

Quellen und Nachweise

ORD-Eintrag
ord-6d14e0d9ea4149c8a12970353c0a690a
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05610154

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