Benzene → N-(4-(4-(Phenylmethyl)-1-piperazinyl)phenyl)acetamide

HRID 1087814

Reaktionsgleichung

Reaktionsgleichung von HRID 1087814
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:28](Cl)(=[O:30])[CH3:29].C1C=CC=CC=1>C(OCC)(=O)C.[OH-].[Na+]>[C:1]1([CH2:7][N:8]2[CH2:9][CH2:10][N:11]([C:14]3[CH:15]=[CH:16][C:17]([NH:20][C:28](=[O:30])[CH3:29])=[CH:18][CH:19]=3)[CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

7

Edukt 4

HCID 241BenzeneHCID 6367Acetyl chloride2×HCID 8471TriethylamineHCID 7372594-(4-Benzylpiperazin-1-yl)aniline

Produkt 1

HCID 960610N-(4-(4-(Phenylmethyl)-1-piperazinyl)phenyl)acetamideAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittel2×HCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

To a solution of 8.5 g (0.03 mole) of the base of 4-[4-(phenylmethyl)-1-piperazinyl)benzeneamine and 16.0 g (0.16 mole) of triethylamine in 450 ml of ethyl acetate was added, dropwise, a solution of 2.5 g (0.035 mole) of acetyl chloride in 50 ml of ethyl acetate. The mixture was magnetically stirred for 3 hr and then heated at reflux for 1 hr. The excess acetyl chloride was co-distilled with benzene and the resulting oil was shaken in 400 ml of 10% sodium hydroxide solution. The suspended tan solid was collected by filtration, washed thrice with 100 ml portions of water, and air dried to give 9.7 g (99%) of crude product. A one gram portion was recrystallized from benzene/petroleum ether to give 100 ml of cream colored solid, m.p. 159°-161° C.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 1 hr
  3. filtrationThe suspended tan solid was collected by filtration
  4. washwashed thrice with 100 ml portions of water, and air
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-dc396a8e47794e67bb832c3e3f9b2130
Quelldatensatz
uspto-grants-1990_10
Patentnummer
US04960776

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