Ammonium Chloride → 1-(Diphenylmethyl)-4-[(2-phenyl-4-methylfuran-5-yl)eth-1-yl]piperazine

HRID 1077845

Reaktionsgleichung

Reaktionsgleichung von HRID 1077845
[C:1]1([C:7]2[O:8][C:9]([CH:13]=O)=[C:10]([CH3:12])[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15]1([CH:21]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH3:34][Mg]I.[Cl-].[NH4+].C(=O)(O)[O-].[Na+]>O.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].C(Cl)Cl.C(OCC)C>[C:15]1([CH:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:28]2[CH2:29][CH2:30][N:31]([CH2:34][CH2:13][C:9]3[O:8][C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[CH:11][C:10]=3[CH3:12])[CH2:32][CH2:33]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

10

Edukt 5

HCID 25517Ammonium ChlorideHCID 70048BenzhydrylpiperazineHCID 516892Sodium BicarbonateHCID 194302672-Phenyl-4-methyl-5-formylfuranHCID 178418373HCID 178418373, Verbindung

Produkt 1

HCID 542165821-(Diphenylmethyl)-4-[(2-phenyl-4-methylfuran-5-yl)eth-1-yl]piperazine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11026Titanium isopropoxideKatalysatorHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 2-phenyl-4-methyl-5-formylfuran (1.1 g), diphenylmethylpiperazine (1.5 g), and titanium(IV)isopropoxide (1.76 g) was stirred for 11/4 hours. Diethyl ether (20 ml) was added, and the resultant solution was stirred for 30 minutes. Methyl magnesium iodide (6 ml of 3M in ether) was then added dropwise, and the mixture stirred at room temperature for 1 hour. Ammonium chloride (20 ml of a saturated solution in water) was then added, followed by 300 ml of methylene chloride, and the mixture made basic with a solution of sodium bicarbonate. The residue was partitioned between methylene chloride/water, the organic layer separated, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was flash-chromatographed on silica gel, eluting with 15% ethyl acetate in heptane with a trace of ammonia, to yield 0.51 g of 1-(diphenylmethyl)-4-[(2-phenyl-4-methylfuran-5-yl)eth-1-yl]piperazine. Treatment with anhydrous hydrochloric acid in ethanol converted the base to its dihydrochloride salt, m.p. 205°-8° C.

Aufarbeitung

  1. customThe residue was partitioned between methylene chloride/water
  2. customthe organic layer separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was flash-chromatographed on silica gel
  7. washeluting with 15% ethyl acetate in heptane with a trace of ammonia

Quellen und Nachweise

ORD-Eintrag
ord-daa25151622044e381d6df788a9c3576
Quelldatensatz
uspto-grants-1996_08
Patentnummer
US05545645

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