Triethylamine → 1-(3-Coumarinylcarbonyl)-4-(3,4,5-trimethoxybenzyl)piperazine

HRID 2108101Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2108101
[O:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]([OH:14])=O)[C:2]1=[O:3].Cl.Cl.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:29]=[C:30]([O:34][CH3:35])[C:31]=1[O:32][CH3:33])[CH2:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N>CCCCCC.C(OCC)(=O)C.O.CN(C)C=O>[O:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]([N:26]2[CH2:25][CH2:24][N:23]([CH2:22][C:21]3[CH:29]=[C:30]([O:34][CH3:35])[C:31]([O:32][CH3:33])=[C:19]([O:18][CH3:17])[CH:20]=3)[CH2:28][CH2:27]2)=[O:14])[C:2]1=[O:3]

Komponenten

9

Edukt 4

HCID 8471TriethylamineHCID 10752Coumarin-3-Carboxylic AcidHCID 76257Diethyl cyanophosphonateHCID 128285011-[(3,4,5-Trimethoxyphenyl)methyl]piperazine;dihydrochloride

Produkt 1

HCID 148497021-(3-Coumarinylcarbonyl)-4-(3,4,5-trimethoxybenzyl)piperazineAusbeute 16,9 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittel2×HCID 6228DimethylformamideLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of coumarin-3-carboxylic acid (0.9 g), 1(3,4,5-trimethoxybenzyl)piperazine dihydrochloride (1.7 g), triethylamine (1.8 g) and N,N-dimethylformamide (20 ml) is added dropwise at room temperature diethyl cyanophosphonate (1.8 ml), followed by stirring for one hour. After addition of water (50 ml), the reaction mixture is left standing for 30 minutes, followed by addition of water (150 ml), ethyl acetate (200 ml) and hexane (50 ml). The mixture is vigorously mixed and the organic layer is separated. The organic layer is washed with water, dried, and concentrated under reduced pressure. The residue is purified by means of a silica gel column chromatography(hexane:acetone=1:1-1:2) to give an oily product, which is crystallized from a mixture of acetone and ethyl ether to afford 1-(3-coumarinylcarbonyl)-4-(3,4,5-trimethoxybenzyl)piperazine (0.35 g) as colorless needles, m.p. 171°-173° C.

Aufarbeitung

  1. waitthe reaction mixture is left
  2. waitstanding for 30 minutes
  3. additionThe mixture is vigorously mixed
  4. customthe organic layer is separated
  5. washThe organic layer is washed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by means of a silica gel column chromatography(hexane:acetone=1:1-1:2)
  9. customto give an oily product, which
  10. customis crystallized from a mixture of acetone and ethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-2fb59b6ff0f84f86af51d2af3a2b22a0
Quelldatensatz
uspto-grants-1990_06
Patentnummer
US04937246

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