1-(4-Fluorobenzoyl)aziridine → N-[2-[4-[(2-benzoxazolyl)amino]-1-piperidinyl]ethyl]-4-fluorobenzamide

HRID 1085692

Reaktionsgleichung

Reaktionsgleichung von HRID 1085692
[F:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([N:8]2[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[NH:13]1[CH2:18][CH2:17][CH:16]([NH:19][C:20]2[O:21][C:22]3[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=3[N:24]=2)[CH2:15][CH2:14]1>CC1C=CC=CC=1>[O:21]1[C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[N:24]=[C:20]1[NH:19][CH:16]1[CH2:17][CH2:18][N:13]([CH2:9][CH2:10][NH:8][C:6](=[O:7])[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:12][CH:11]=2)[CH2:14][CH2:15]1

Komponenten

4

Edukt 2

HCID 848531-(4-Fluorobenzoyl)aziridineHCID 14575294N-(4-piperidinyl)-2-benzoxazolamine

Produkt 1

HCID 15725198N-[2-[4-[(2-benzoxazolyl)amino]-1-piperidinyl]ethyl]-4-fluorobenzamideAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 1.65 parts of 1-(4-fluorobenzoyl)aziridine (solution in benzene 1.2M), 2.1 parts of N-(4-piperidinyl)-2-benzoxazolamine and 90 parts of methylbenzene was stirred and refluxed overnight. The reaction mixture was evaporated and the residue was crystallized from 2-propanol. The product was filtered off and recrystallized from 2-propanone, yielding 1.3 parts (34%) of N-[2-[4-[(2-benzoxazolyl)-amino]-1-piperidinyl]ethyl]-4-fluorobenzamide; mp. 173.3° C. (448).

Aufarbeitung

  1. temperaturerefluxed overnight
  2. customThe reaction mixture was evaporated
  3. customthe residue was crystallized from 2-propanol
  4. filtrationThe product was filtered off
  5. customrecrystallized from 2-propanone

Quellen und Nachweise

ORD-Eintrag
ord-587d920b336a4dbaa99afdb1e2c4c323
Quelldatensatz
uspto-grants-1991_04
Patentnummer
US05010198

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