Toluene → HCID 12852070, Verbindung

HRID 1248246Notizen

Reaktionsgleichung

[NH2:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][CH:12]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:11][CH2:10]1)=[O:5].C(OC(=O)C)(=[O:29])C.C[C:35]1[CH:40]=CC=CC=1>>[F:22][C:19]1[CH:18]=[CH:17][C:16]([C:15]([CH:12]2[CH2:13][CH2:14][N:9]([CH2:8][CH2:7][N:6]3[C:4](=[O:5])[C:3]4[C:2](=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:1]=[C:40]3[CH3:35])[CH2:10][CH2:11]2)=[O:29])=[CH:21][CH:20]=1

Komponenten

Edukt 3

HCID 1140Toluene

HCID 7918Acetic Anhydride

HCID 20278972HCID 20278972, Verbindung

Produkt 1

HCID 12852070HCID 12852070, VerbindungAusbeute 69 %

Versuchsvorschrift

A mixture of 6 parts of 2-amino-N-[2-[4-(4-fluorobenzyl)-1-piperidinyl]ethyl]benzamide, 10 parts of acetic acid anhydride and 108 parts of methylbenzene is stirred and refluxed overnight. The reaction mixture is evaporated and water is added to the oily residue. The whole is alkalized with a dilute sodium hydroxide solution and extracted with trichloromethane. The extract is dried, filtered and evaporated. The oily residue is crystallized from a mixture of 4-methyl-2-pentanone and 2,2'-oxybispropane. The product is filtered off and recrystallized from 2-propanol, yielding 4.4 parts (69%) of 3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2-methyl-4(3H)-quinazolinone; mp. 164.9° C.

Aufarbeitung

temperaturerefluxed overnight
customThe reaction mixture is evaporated
additionwater is added to the oily residue
extractionextracted with trichloromethane
customThe extract is dried
filtrationfiltered
customevaporated
customThe oily residue is crystallized from a mixture of 4-methyl-2-pentanone and 2,2'-oxybispropane
filtrationThe product is filtered off
customrecrystallized from 2-propanol

Quellen und Nachweise

ORD-Eintrag: ord-a443e8299cae40e18de1e0158759117c
Quelldatensatz: uspto-grants-1985_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04522945

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