Cyclooctylamine → HCID 20375715, compound

HRID 1448799Notes

Reaction equation

HRID 1448799 reaction equation
C1(N)CCCCCCC1.CCC(C(Cl)=O)=O.[CH:17]1([NH:25][C:26](=[O:32])[C:27]([O:29]CC)=[O:28])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.[Na]>C(Cl)(Cl)Cl.C(O)C>[CH:17]1([NH:25][C:26](=[O:32])[C:27]([OH:29])=[O:28])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 2903CyclooctylamineHCID 5360545SodiumHCID 11007880Butanoyl chloride, 2-oxo-HCID 17256705HCID 17256705, compound

Product 1

HCID 20375715HCID 20375715, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6212ChloroformSolvent2×

Conditions

Temperature
10 °C

Procedure

To a solution of cyclooctylamine (12.7 g., 0.10 mole) in chloroform (50 ml.) at 10°-20° C. is added dropwise ethyloxalyl chloride (6.83 g., 0.05 mole) in chloroform (50 ml.) over a period of 30 minutes. After stirring for 2 additional hours at 10° C., the mixture is washed with H2O (4×50 ml.), and the organic layer dried over Na2SO4. After filtration and evaporation an oil is obtained (11.3 g.). To the crude ethyl N-cyclooctyloxamate dissolved in ethanol (27 ml.) is added sodium (1.15 g., 0.05 mole) dissolved in absolute ethanol (35 ml.) and the mixture is stirred overnight. Following evaporation, the residue is dissolved in H2O (41 ml.) with heating, and the solution filtered while hot. The filtrate is acidified with 6 N HCl, and the resulting slurry cooled at ice temperature. The solid obtained by filtration is recrystallized from boiling H2O (100 ml.) to give N-cyclooctyloxamic acid, m.p. 115°-116° C.

Workup

  1. washthe mixture is washed with H2O (4×50 ml.)
  2. dry with materialthe organic layer dried over Na2SO4
  3. filtrationAfter filtration and evaporation an oil
  4. customis obtained (11.3 g.)
  5. stirringthe mixture is stirred overnight
  6. customevaporation
  7. dissolutionthe residue is dissolved in H2O (41 ml.)
  8. temperaturewith heating
  9. filtrationthe solution filtered while hot
  10. temperaturethe resulting slurry cooled at ice temperature
  11. customThe solid obtained by filtration
  12. customis recrystallized

Sources & evidence

ORD record
ord-f42e51cc3fda4ec7a32c77e8142c9073
Source dataset
uspto-grants-1980_02
Patent number
US04187315

Reaction notes

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