Diisopropylethylamine → 1-(2-(4-Benzyl-piperazin-1-yl)-ethyl)-3-(2,4,6-trimethyl-3-piperidin-1-yl-phenyl)-urea

HRID 1182252Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1182252
[CH3:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12]N[CH2:10][CH2:9]2)=[C:6]([CH3:14])[CH:5]=[C:4]([CH3:15])[C:3]=1[NH2:16].[CH3:17]CN(C(C)C)C(C)C.ClC(Cl)(O[C:30](=[O:36])OC(Cl)(Cl)Cl)Cl.[CH2:38]([N:45]1[CH2:50][CH2:49][N:48]([CH2:51][CH2:52][NH2:53])[CH2:47][CH2:46]1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>ClCCCl>[CH2:38]([N:45]1[CH2:46][CH2:47][N:48]([CH2:51][CH2:52][NH:53][C:30]([NH:16][C:3]2[C:4]([CH3:15])=[CH:5][C:6]([CH3:14])=[C:7]([N:8]3[CH2:9][CH2:10][CH2:17][CH2:12][CH2:13]3)[C:2]=2[CH3:1])=[O:36])[CH2:49][CH2:50]1)[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 27353312-(4-Benzylpiperazin-1-yl)ethan-1-amineHCID 47388012,4,6-Trimethyl-3-piperazin-1-yl-phenylamine

Produkt 1

HCID 596437401-(2-(4-Benzyl-piperazin-1-yl)-ethyl)-3-(2,4,6-trimethyl-3-piperidin-1-yl-phenyl)-ureaAusbeute 166,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 2,4,6-trimethyl-3-piperazin-1-yl-phenylamine (0.2 g, 0.92 mmol) and Hunig's base (0.7 mL, 4.0 mmol) in anhydrous 1,2-dichloroethane (3 mL) at 0° C. was added triphosgene (0.1 g, 0.35 mmol). The mixture was stirred at 0° C. for 30 minutes before the addition of a solution of 2-(4-benzyl-piperazin-1-yl)-ethylamine (0.2 g, 0.92 mmol) in 1,2-dichloroethane (2 mL). The reaction was stirred overnight and partitioned between water and methylene chloride. The organic layer was washed with brine, dried (MgSO4) and concentrated. The residue was chromatographed with florisil, eluting with a mixture of hexanes and ethyl acetate in the ratio of 2:1 to 100% ethyl acetate, and then to a mixture of ethyl acetate and MeOH (30:1) to give the title compound as a white foam (0.27 g, 64% yield).

Aufarbeitung

  1. custompartitioned between water and methylene chloride
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was chromatographed with florisil
  6. washeluting with a mixture of hexanes and ethyl acetate in the ratio of 2
  7. addition1 to 100% ethyl acetate, and then to a mixture of ethyl acetate and MeOH (30:1)

Quellen und Nachweise

ORD-Eintrag
ord-647dc391e7c048a580a2738a8fa06a34
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07288538B2

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