Potassium Carbonate → cis-4-[4-(4-Cyclobutylmethylpiperazin-1-yl)-3-(4,4-dimethylcyclohexyl)phenyl]-2,6-dimethylmorpholine

HRID 32180

Reaktionsgleichung

Reaktionsgleichung von HRID 32180
[CH3:1][C:2]1([CH3:28])[CH2:7][CH2:6][CH:5]([C:8]2[CH:9]=[C:10]([N:20]3[CH2:25][C@H:24]([CH3:26])[O:23][C@H:22]([CH3:27])[CH2:21]3)[CH:11]=[CH:12][C:13]=2[N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH2:4][CH2:3]1.Br[CH2:30][CH:31]1[CH2:34][CH2:33][CH2:32]1.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+]>C(OCC)(=O)C.CN(C)C=O>[CH:31]1([CH2:30][N:17]2[CH2:16][CH2:15][N:14]([C:13]3[CH:12]=[CH:11][C:10]([N:20]4[CH2:25][C@H:24]([CH3:26])[O:23][C@H:22]([CH3:27])[CH2:21]4)=[CH:9][C:8]=3[CH:5]3[CH2:4][CH2:3][C:2]([CH3:28])([CH3:1])[CH2:7][CH2:6]3)[CH2:19][CH2:18]2)[CH2:34][CH2:33][CH2:32]1

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 2734658(Bromomethyl)cyclobutane2×HCID 59769447cis-4-[3-(4,4-Dimethylcyclohexyl)-4-piperazin-1-ylphenyl]-2,6-dimethylmorpholine

Produkt 1

HCID 59769406cis-4-[4-(4-Cyclobutylmethylpiperazin-1-yl)-3-(4,4-dimethylcyclohexyl)phenyl]-2,6-dimethylmorpholine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of the cis-4-[3-(4,4-dimethylcyclohexyl)-4-piperazin-1-ylphenyl]-2,6-dimethylmorpholine (30 mg, 0.0778 mmol) produced in Example (61b), bromomethylcyclobutane (23 mg, 0.156 mmol), potassium carbonate (22 mg, 0.156 mmol) and dimethylformamide (1 mL) was stirred for 1 hour at an external temperature of 80° C. Then, bromomethylcyclobutane (23 mg, 0.156 mmol) was further added and stirring was continued for 2 hours under the same conditions. Saturated aqueous solution of sodium hydrogencarbonate was added to the reaction mixture and extraction was performed with ethyl acetate. The separated organic layer was washed with water and brine in that order, and then the solvent was distilled off by nitrogen stream. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/hexane) to give cis-4-[4-(4-cyclobutylmethylpiperazin-1-yl)-3-(4,4-dimethylcyclohexyl)phenyl]-2,6-dimethylmorpholine as a colorless oil.

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for 2 hours under the same conditions
  3. washThe separated organic layer was washed with water and brine in that order
  4. distillationthe solvent was distilled off by nitrogen stream
  5. customThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-3f4e50d52dd443b886a52577dddca29c
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425554B2

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