Potassium Carbonate → HCID 66758298, Verbindung

HRID 457103Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 457103
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([O:16][CH3:17])[CH2:13][CH2:12][NH:11][CH2:10][C:9]2([CH3:15])[OH:14])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][CH2:26][CH:27]=[C:28]1[C:34]2[CH:35]=[CH:36][CH:37]=[N:38][C:33]=2[CH2:32][O:31][C:30]2[CH:39]=[CH:40][C:41]([C:43]([OH:46])([CH3:45])[CH3:44])=[CH:42][C:29]1=2>C(#N)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([O:16][CH3:17])[CH2:13][CH2:12][N:11]([CH2:25][CH2:26][CH:27]=[C:28]3[C:34]4[CH:35]=[CH:36][CH:37]=[N:38][C:33]=4[CH2:32][O:31][C:30]4[CH:39]=[CH:40][C:41]([C:43]([OH:46])([CH3:45])[CH3:44])=[CH:42][C:29]3=4)[CH2:10][C:9]2([CH3:15])[OH:14])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 231368654-(4-Chlorophenyl)-4-methoxy-3-methyl-3-piperidinolHCID 666859992-[5-(3-Bromo-propylidene)-5,1 1-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yl]-propan-2-ol

Produkt 1

HCID 66758298HCID 66758298, VerbindungAusbeute 37,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 18373917Acetonitrile--water (1/1)Lösungsmittel

Versuchsvorschrift

To a solution of 4-(4-chloro-phenyl)-4-methoxy-3-methyl-piperidin-3-ol (206 mg, 1.24 mmol) in acetonitrile/water (4:1, 20 mL) was added potassium carbonate (171 mg, 1.24 mmol) followed by 2-[5-(3-bromo-propylidene)-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yl]-propan-2-ol (417 mg, 1.12 mmol). The mixture was stirred at rt 40 h and concentrated. The product residue was partitioned between ethyl acetate and water and the organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography (100% methylene chloride−90% methylene chloride/10% methanol gradient) to afford the titled compound (232 mg, 35%) as an off-white solid.

Aufarbeitung

  1. concentrationconcentrated
  2. customThe product residue was partitioned between ethyl acetate and water
  3. washthe organic phase was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel chromatography (100% methylene chloride−90% methylene chloride/10% methanol gradient)

Quellen und Nachweise

ORD-Eintrag
ord-5ccac15cf63749fb90b62c4eb2446574
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07186729B2

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