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

HRID 1065824Notes

Reaction equation

HRID 1065824 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent3×HCID 8471TriethylamineSolvent

Conditions

Temperature
5 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b3bab630e70a4a28beae6480d609308d
Source dataset
uspto-grants-1982_05
Patent number
US04331683

Reaction notes

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