Cyclooctanone → 1-Cyclooctylpyrrolidine

HRID 1263381Notes

Reaction equation

HRID 1263381 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 was 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 was added and the mixture was mechanically stirred and heated at reflux (the reaction was monitored by NMR analysis) for 108 hours. The reaction mixture was filtered through a fritted glass funnel. The filtrate was 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 were acceptable for the desired product, 1-(1-pyrrolino)cyclooctene. Saturation of the 1-(1-pyrrolino)cyclooctene to give N-cyclooctylpyrrolidine was 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 was charged with 75 gm
  2. temperatureheated
  3. temperatureat reflux (the reaction
  4. customfor 108 hours
  5. filtrationThe reaction mixture was filtered through a fritted glass funnel
  6. concentrationThe filtrate was concentrated at reduced pressure on a rotary evaporator
  7. customto give 70.5 gm

Sources & evidence

ORD record
ord-83672f95bc0349c5924da434cd80475a
Source dataset
uspto-grants-2003_04
Patent number
US06540905B1

Reaction notes

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