Oxalyl chloride → 1-(Indole-5-carbonyl)-4-phenethylpiperazine

HRID 1086854

Reaktionsgleichung

Reaktionsgleichung von HRID 1086854
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C(Cl)(=O)C(Cl)=O.[CH2:19]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(C(C)C)CC)(C)C>C1COCC1.CN(C=O)C.ClCCl>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([N:30]3[CH2:31][CH2:32][N:27]([CH2:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:28][CH2:29]3)=[O:12])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Komponenten

8

Edukt 4

HCID 65578Oxalyl chlorideHCID 742801H-Indole-5-Carboxylic AcidHCID 792141-PhenethylpiperazineHCID 81531Diisopropylethylamine

Produkt 1

HCID 149859971-(Indole-5-carbonyl)-4-phenethylpiperazine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Indole-5-carboxylic acid (57 mg, 0.35 mmol) was dissolved in THF(2 ml) and DMF (1 drop), then oxalyl chloride (37 μl, 54 mg, 0.42 mmol) was added. The mixture was stirred at room temperature for 3 hours, the solvent was evaporated under reduced pressure and the residue was dissolved in DMF (2 ml) and added to a stirred solution of 1-phenethylpiperazine (66 mg, 0.35 mmol) and diisopropylethylamine (91 μl, 68 mg, 0.52 mmol) in dichloromethane (1 ml). The mixture was stirred at room temperature for 24 hours, then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with CH2Cl2 /CH3OH/NH3 ; 95:5:0.5 and crystallized from EtOAc/hexane to give the piperazine as microcrystals (32 mg, 27%), mp 105°-108° C. δH (CDCl3) 8.47(1H, br s), 7.73(1H, s), 7.38(1H, d J 8.4 Hz), 7.32-7.19(7H, m), 6.56(1H, br s), 3.7(4H, br s), 2.81(2H, m), 2.65(2H, m), and 2.6(4H, br s).

Aufarbeitung

  1. customthe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in DMF (2 ml)
  3. stirringThe mixture was stirred at room temperature for 24 hours
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica gel
  6. washeluting with CH2Cl2 /CH3OH/NH3
  7. custom95:5:0.5 and crystallized from EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-c62a4b98bde34dbd84a8225a42a4089e
Quelldatensatz
uspto-grants-1991_07
Patentnummer
US05032598

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