Cyclooctanone → 1-Cyclooctylpyrrolidine

HRID 1167038Notes

Reaction equation

HRID 1167038 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:6]1(=O)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.S([O-])([O-])(=O)=O.[Mg+2]>CCCCCC>[CH:6]1([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 10403CyclooctanoneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 31268Pyrrolidine

Product 1

HCID 232778741-Cyclooctylpyrrolidine

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A three-neck 3000 ml. flask is charged with 75 gm. (1.05 moles) of pyrrolidine, 51 gm. cyclooctanone (0.4 mole) and 80 ml. anhydrous hexane. To the resulting solution, 80 gm. (0.8 mole) of anhydrous magnesium sulfate is added and the mixture is mechanically stirred and heated at reflux (the reaction was monitored by NMR analysis) for 108 hours. The reaction mixture is filtered through a fritted glass funnel. The filtrate is concentrated at reduced pressure on a rotary evaporator to give 70.5 gm. of a clear (yellow-tinted) oily substance. 1H-NMR and 13C-NMR spectra are acceptable for the desired product, 1-(1-pyrrolino)cyclooctene. Saturation of the 1-(1-pyrrolino)cyclooctene to give N-cyclooctylpyrrolidine is accomplished in 98% yield by catalytic hydrogenation in ethanol at a 55 psi pressure of hydrogen gas in the presence of 10% Pd on activated carbon.

Workup

  1. additionflask is charged with 75 gm
  2. temperatureheated
  3. temperatureat reflux (the reaction
  4. customfor 108 hours
  5. filtrationThe reaction mixture is filtered through a fritted glass funnel
  6. concentrationThe filtrate is concentrated at reduced pressure on a rotary evaporator
  7. customto give 70.5 gm

Sources & evidence

ORD record
ord-71e7e88011f04d04a78be62ce6731b97
Source dataset
uspto-grants-2003_09
Patent number
US06616911B2

Reaction notes

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