2-(4-Chlorophenoxy)aniline → 1-Acetyl-N-(2-(1-(2-(4-chlorophenoxy)phenylamino)ethyl)phenyl)piperidine-4-carboxamide

HRID 1043030

Reaktionsgleichung

Reaktionsgleichung von HRID 1043030
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[NH2:9])=[CH:4][CH:3]=1.[C:16]([N:19]1[CH2:24][CH2:23][CH:22]([C:25]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:34](=O)[CH3:35])=[O:26])[CH2:21][CH2:20]1)(=[O:18])[CH3:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCl.C(O)(=O)C.[Cl-].C(O[Ti+](OC(C)C)OC(C)C)(C)C>[C:16]([N:19]1[CH2:24][CH2:23][CH:22]([C:25]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[CH:34]([NH:9][C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[O:6][C:5]2[CH:14]=[CH:15][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH3:35])=[O:26])[CH2:21][CH2:20]1)(=[O:18])[CH3:17]

Komponenten

8

Edukt 4

HCID 760102-(4-Chlorophenoxy)anilineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 171457861-acetyl-N-(2-acetylphenyl)piperidine-4-carboxamide

Produkt 1

HCID 426136031-Acetyl-N-(2-(1-(2-(4-chlorophenoxy)phenylamino)ethyl)phenyl)piperidine-4-carboxamideAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidKatalysatorHCID 3084342Chlorotitanium triisopropoxideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-(4-Chlorophenoxy)aniline (25 mg, 0.1138 mmol, 1.1 eq) and 1-acetyl-N-(2-acetylphenyl)piperidine-4-carboxamide (30 mg, 0.1040 mmol, 1 eq) were stirred in dry dichloromethane (DCM) at room temperature for 10 min. Tri-isopropoxytitanium chloride (55 μL, 0.2303 mmol, 2.2 eq) was added to the reaction mixture which was stirred at room temperature for an additional 10 min. Sodium triacetoxyborohydride (110 mg, 0.5190 mmol, 5 eq) and acetic acid (3 drops) were added to the reaction mixture which was stirred at room temperature for 16 h. The reaction mixture was then poured onto a solution of saturated aqueous sodium bicarbonate (50 mL) and extracted with DCM (30 mL). The organic layer was washed with brine (50 mL), dried over MgSO4, filtered and concentrated to give the crude as a yellow oil. Purification of the crude by flash chromatography (ISCO) eluting with a gradient [from 100% petroleum ether (PE) to 100% EtOAc] gave the title compound (5 mg, 10%) as a clear oil.

Aufarbeitung

  1. stirringwas stirred at room temperature for 16 h
  2. extractionextracted with DCM (30 mL)
  3. washThe organic layer was washed with brine (50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude as a yellow oil
  8. customPurification of the crude by flash chromatography (ISCO)
  9. washeluting with a gradient [from 100% petroleum ether (PE) to 100% EtOAc]

Quellen und Nachweise

ORD-Eintrag
ord-9efb7f91417d4f318acce73adabc7f10
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08558028B2

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