Cyclohexanone → 1-Cyclohexylpyrrolidine

HRID 514644Notes

Reaction equation

HRID 514644 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:6]1(=O)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[O-]S([O-])(=O)=O.[Mg+2]>C1CCCCC1>[CH:6]1([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 7967Cyclohexanone2×HCID 24083Sulfuric acid magnesium salt (1:1)HCID 31268Pyrrolidine

Product 1

HCID 1390641-CyclohexylpyrrolidineYield 91%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

Cyclohexylpyrrolidine was prepared as described in the procedure below illustrated in Scheme 1. In a 3-neck reaction flask equipped with a mechanical stirrer and heating mantle, a 2 molar equivalent of pyrrolidine were mixed with 1 molar equivalent of cyclohexanone in dry cyclohexane to make a 1M solution with respect to the cyclohexanone. To the mixture, 2 molar equivalents of anhydrous MgSO4 (as dehydrating agent) were added. The resulting mixture was refluxed for 94 hours. The progress of the reaction was monitored by NMR analysis.

Workup

  1. customIn a 3-neck reaction flask equipped with a mechanical stirrer
  2. temperatureheating mantle
  3. temperatureThe resulting mixture was refluxed for 94 hours

Sources & evidence

ORD record
ord-b7724158c78141338e8d3ee33dce76d4
Source dataset
uspto-grants-2015_08
Patent number
US09108856B2

Reaction notes

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