Triphenylphosphine → HCID 22154693, Verbindung

HRID 1382217Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1382217
N(C(OCC)=O)=NC(OCC)=O.[F:13][C:14]1[C:19]([F:20])=[CH:18][C:17]([N+:21]([O-:23])=[O:22])=[CH:16][C:15]=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:44]([N:51]1[CH2:56][CH2:55][N:54]([CH2:57][C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)[CH2:53][CH:52]1[CH2:64][OH:65])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>C1COCC1>[CH2:44]([N:51]1[CH2:56][CH2:55][N:54]([CH2:57][C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)[CH2:53][CH:52]1[CH2:64][O:65][C:18]1[C:17]([N+:21]([O-:23])=[O:22])=[CH:16][CH:15]=[C:14]([F:13])[C:19]=1[F:20])[C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10827800(1,4-Dibenzylpiperazin-2-yl)methanolHCID 221546562,3-Difluoro-5-nitrophenol

Produkt 1

HCID 22154693HCID 22154693, VerbindungAusbeute 6.043,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

(1Ba) A solution of 4.7 g (27 mmol) of diethyl azodicarboxylate in 15 ml of THF was added dropwise at 15° C. while stirring to a solution of 3.9 g (22.5 mmol) of 2,3-difluoro-5-nitrophenol, 7.1 g (27 mmol) of triphenylphosphine and 8 g (0.27 mmol) of 1,4-dibenzyl-2-hydroxymethylpiperazine in 250 ml of THF. The yellow reaction solution was then stirred at room temperature for an additional 3 hours. After concentrating the reaction solution, the oily residue was stirred with a total of 2 l of hot n-hexane in several portions. The hexane solution was separated and cooled. The separated triphenylphosphine oxide was removed by filtration under suction, and the filtrate was concentrated. Chromatography on silica gel with ether/n-hexane (1:1) as the eluent gave 7.4 g of 1,4-dibenzyl-2-[(6-nitro-2,3-difluorophenoxy)methyl]piperazine as a brown oil.

Aufarbeitung

  1. concentrationAfter concentrating the reaction solution
  2. stirringthe oily residue was stirred with a total of 2 l of hot n-hexane in several portions
  3. customThe hexane solution was separated
  4. temperaturecooled
  5. customThe separated triphenylphosphine oxide was removed by filtration under suction
  6. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-99272be9bdb74761ac5184e3523cd5e3
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04806541

Notizen zur Reaktion

Wird geladen…