Octylamine → trans-N-Octyl-2-(4-nitrophenyl)cyclopropanecarboxamide

HRID 66814

Reaktionsgleichung

Reaktionsgleichung von HRID 66814
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]2[CH2:12][C@H:11]2[C:13]([OH:15])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].ClC(OCC)=O.[CH2:22]([NH2:30])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:22]([NH:30][C:13]([C@@H:11]1[CH2:12][C@H:10]1[C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)=[O:15])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Komponenten

6

Edukt 3

HCID 8143OctylamineHCID 10928Ethyl chloroformateHCID 12854631rac-(1R,2R)-2-(4-nitrophenyl)cyclopropane-1-carboxylic acid

Produkt 1

HCID 12854633trans-N-Octyl-2-(4-nitrophenyl)cyclopropanecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittel3×HCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

To a stirred slurry of 4.1 g. of trans-2-(4-nitrophenyl)cyclopropanecarboxylic acid in 50 ml. of chloroform was added 2.2 g. of triethylamine. The clear solution thus obtained was cooled to ca. 5° C., and a solution of 2.4 g. of ethyl chloroformate in 15 ml. of chloroform was added dropwise with stirring during 15 minutes. Stirring was continued for 20 minutes, and then a solution of 2.8 g. of octylamine in 15 ml. of chloroform was added dropwise with stirring, at 0°-5° C., during 10-15 minutes. The cooling bath was removed, and stirring was continued for 1 hour. At this point, the solvent was removed by evaporation in vacuo, and the residue was triturated under a mixture of 70 ml. of water and 15 ml. of ethanol. The solid which remained out of solution was recovered by filtration, washed with water, and dried, to give 6.2 g. of the title compound as a white solid, m.p. 126° -129° C.

Aufarbeitung

  1. customThe clear solution thus obtained
  2. stirringStirring
  3. waitwas continued for 20 minutes
  4. stirringwith stirring, at 0°-5° C., during 10-15 minutes
  5. customThe cooling bath was removed
  6. stirringstirring
  7. waitwas continued for 1 hour
  8. customAt this point, the solvent was removed by evaporation in vacuo
  9. customthe residue was triturated under a mixture of 70 ml
  10. filtrationwas recovered by filtration
  11. washwashed with water
  12. customdried
  13. customto give 6.2 g

Quellen und Nachweise

ORD-Eintrag
ord-392ee65cf4244ebc867e6abbcd49cb68
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04343813

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