Benzylamine → N-Benzyl-2-phenylacrylamide

HRID 1742597Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1742597
[C:1]([OH:11])(=O)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:3].CN1CCOCC1.C(OC(Cl)=O)C(C)C.[CH2:27]([NH2:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O1CCCC1.CCOCC>[C:4]1([C:2](=[CH2:3])[C:1]([NH:34][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:11])[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Komponenten

7

Edukt 4

HCID 7504BenzylamineHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 68114Atropic acid

Produkt 1

HCID 54041249N-Benzyl-2-phenylacrylamideAusbeute 44,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A stirred solution of atropic acid (10.3 g, 69.5 mmol) in dry tetrahydrofuran (100 ml) was treated under nitrogen with N-methylmorpholine (7.7 ml, 70.0 mmol), cooled to -10°, treated dropwise with iso-butylchloroformate (9 ml, 69.4 mmol), treated dropwise with benzylamine (7.6 ml, 69.6 mmol), warmed to room temperature over 1 hour, filtered and evaporated in vacuo to give a yellow oil which was dissolved in ether (100 ml). The solution was washed with 0.1N-HCl (200 ml), brine (100 ml), 0.1N-NaOH (100 ml) and brine (100 ml), dried (MgSO4), and evaporated in vacuo to give a yellow liquid. Purification by chromatography (silica; di-iso-propyl ether) gave the product as white crystals (7.3 g), m.p. 84°-86° (from di-iso-propyl ether).

Aufarbeitung

  1. temperaturecooled to -10°
  2. filtrationfiltered
  3. customevaporated in vacuo
  4. customto give a yellow oil which
  5. washThe solution was washed with 0.1N-HCl (200 ml), brine (100 ml), 0.1N-NaOH (100 ml) and brine (100 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo
  8. customto give a yellow liquid
  9. customPurification by chromatography (silica; di-iso-propyl ether)

Quellen und Nachweise

ORD-Eintrag
ord-cbc28da0376c4601a872ab0b19863330
Quelldatensatz
uspto-grants-1994_08
Patentnummer
US05340812

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