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Hydrochloric Acid → 1-(2-Indanylcarbonyl)-4-(3,4,5-trimethoxybenzyl)-piperazine hydrochloride

HRID 1638794
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Reaktionsgleichung

Reaktionsgleichung von HRID 1638794
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[C:10]([OH:12])=O.C1C2C(=CC=CC=2)CC1C([Cl:24])=O.S(Cl)(Cl)=O.Cl.Cl.[CH3:31][O:32][C:33]1[CH:34]=[C:35]([CH:43]=[C:44]([O:48][CH3:49])[C:45]=1[O:46][CH3:47])[CH2:36][N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1.Cl>C1(C)C=CC=CC=1.CO.C(OCC)(=O)C.O.CN(C)C=O.C(N(CC)CC)C>[ClH:24].[CH2:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1][CH:2]1[C:10]([N:40]1[CH2:39][CH2:38][N:37]([CH2:36][C:35]2[CH:43]=[C:44]([O:48][CH3:49])[C:45]([O:46][CH3:47])=[C:33]([O:32][CH3:31])[CH:34]=2)[CH2:42][CH2:41]1)=[O:12]
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Komponenten

12

Edukt 5

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 5757772-Indancarboxylic AcidHCID 128285011-[(3,4,5-Trimethoxyphenyl)methyl]piperazine;dihydrochlorideHCID 213133822,3-dihydro-1H-indene-2-carbonyl chloride

Produkt 1

HCID 19841202
1-(2-Indanylcarbonyl)-4-(3,4,5-trimethoxybenzyl)-piperazine hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 6

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

In a manner as that described in Example 5, 2-indane carboxylic acid (0.8 g) is converted to the 2-indane carbonyl chloride by using thionyl chloride (2 ml) in toluene (10 ml). The product thus obtained is added to a mixture of 1-(3,4,5-trimethoxybenzyl)piperazine dihydrochloride (2.1 g), triethylamine (5.9 g) and N,N-dimethylformamide (20 ml). The whole mixture is left standing at room temperature for two hours. A mixture of water (300 ml) and ethyl acetate (300 ml) is added to the mixture, and the mixture is shaken thoroughly. The organic layer is separated, washed with water, dried and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (hexane:acetone=1:1) to give an oily product, which is converted to the hydrochloride in a mixture of methanol and ethyl acetate to give 1-(2-indanylcarbonyl)-4-(3,4,5-trimethoxybenzyl)-piperazine hydrochloride (1.1 g) as colorless crystals, m.p. 227°-232° C. (decomp.).

Aufarbeitung

  1. customThe product thus obtained
  2. waitThe whole mixture is left
  3. additionis added to the mixture
  4. customThe organic layer is separated
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by silica gel column chromatography (hexane:acetone=1:1)
  9. customto give an oily product, which

Quellen und Nachweise

ORD-Eintrag
ord-b3ad8c61b3d04cc79b38144376a4cb1b
Quelldatensatz
uspto-grants-1989_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04880809

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