4-Methylmorpholine → Methyl 2-[3-[(4'-chlorobiphenyl-4-yl)carbonylaminomethyl]piperidin-1-yl]benzoate

HRID 602166

Reaktionsgleichung

Reaktionsgleichung von HRID 602166
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([O:13][CH3:14])=[O:12])[CH2:4]1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][C:29]([C:32](O)=[O:33])=[CH:28][CH:27]=2)=[CH:22][CH:21]=1.O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([NH:1][CH2:2][CH:3]3[CH2:8][CH2:7][CH2:6][N:5]([C:9]4[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=4[C:11]([O:13][CH3:14])=[O:12])[CH2:4]3)=[O:33])=[CH:28][CH:27]=2)=[CH:24][CH:25]=1

Komponenten

7

Edukt 5

HCID 79724-MethylmorpholineHCID 6160024-Biphenylcarboxylic acid, 4'-chloro-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 58992630Methyl 2-[3-(aminomethyl)piperidin-1-yl]benzoate

Produkt 1

HCID 58992643Methyl 2-[3-[(4'-chlorobiphenyl-4-yl)carbonylaminomethyl]piperidin-1-yl]benzoateAusbeute 76,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Methyl 2-[3-(aminomethyl)piperidin-1-yl]benzoate (78.2 mg, 0.315 mmol) was dissolved in N,N-dimethylformamide (3 mL) and the solution was chilled to 0° C. While this solution was stirred, 4′-chlorobiphenyl-4-carboxylic acid (81.1 mg, 0.349 mmol), 1-hydroxybenzotriazole monohydrate (54.1 mg, 0.353 mmol), N-methylmorpholine (90 μL, 0.819 mmol) and 3-(3-dimethylaminopropyl)-1-ethylcarbodiimide hydrochloride (64.6 mg, 0.337 mmol) were added and the mixture was stirred for 20 min. The reaction mixture was then stirred at room temperature for 12 hours. Subsequently, the mixture was extracted with ethyl acetate and the organic layer washed sequentially with 5% aqueous citric acid, a saturated aqueous sodium bicarbonate solution, water and brine. The washed product was dried over anhydrous sodium sulfate and the solvent was concentrated. Purification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=2:1) gave 111 mg (76%) of the desired compound as a colorless powder.

Aufarbeitung

  1. stirringthe mixture was stirred for 20 min
  2. stirringThe reaction mixture was then stirred at room temperature for 12 hours
  3. extractionSubsequently, the mixture was extracted with ethyl acetate
  4. washthe organic layer washed sequentially with 5% aqueous citric acid
  5. dry with materialThe washed product was dried over anhydrous sodium sulfate
  6. concentrationthe solvent was concentrated
  7. customPurification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-7ab5bbb423f743089bb67d9ae916b2ca
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902367B2

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