1-Chloro-4-(chloromethyl)benzene → 3-Carbamoyl-1-(4-chlorobenzyl)piperidine

HRID 1280989

Reaktionsgleichung

Reaktionsgleichung von HRID 1280989
[NH:1]1[CH2:9][CH2:8][CH2:7][CH:3]([C:4]([NH2:6])=[O:5])[CH2:2]1.CCN(CC)CC.[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Cl)=[CH:20][CH:19]=1.C([O-])(O)=O.[Na+]>CC#N.C(O)C.O>[C:4]([CH:3]1[CH2:7][CH2:8][CH2:9][N:1]([CH2:22][C:21]2[CH:24]=[CH:25][C:18]([Cl:17])=[CH:19][CH:20]=2)[CH2:2]1)(=[O:5])[NH2:6]

Komponenten

8

Edukt 4

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 8471TriethylamineHCID 929803-PiperidinecarboxamideHCID 516892Sodium Bicarbonate

Produkt 1

HCID 28457973-Carbamoyl-1-(4-chlorobenzyl)piperidineAusbeute 55,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of nipecotamide (6.40 g, 50 mmol) in CH3CN (150 mL) and ethanol (20 mL) was treated with Et3N (7.0 mL, 50 mmol) and 4-chlorobenzyl chloride (8.05 g, 50 mmol). The reaction mixture was stirred at 50° C. for 16 h. After cooling to room temperature, saturated aqueous NaHCO3 (50 mL) and water (150 mL) was added to the reaction mixture. The mixture was extracted with ethyl acetate (150 mL×3) and the combined organic layers were washed with brine, dried (Na2SO4) and concentrated to give a pale red solid. The crude solid was washed with ether (100 mL) to afford 3-carbamoyl-1-(4-chlorobenzyl)piperidine (6.98 g, 54%).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. extractionThe mixture was extracted with ethyl acetate (150 mL×3)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto give a pale red solid
  7. washThe crude solid was washed with ether (100 mL)

Quellen und Nachweise

ORD-Eintrag
ord-8f36a84adc9b485faf9c12452aabe87d
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06451842B1

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