Cyclohexane → HCID 21695009, compound

HRID 2372315Notes

Reaction equation

HRID 2372315 reaction equation
[H-].[Na+].[C:3]1(=[O:9])[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1.Cl.[N:11]1[CH:16]=[CH:15][C:14]([CH2:17]Cl)=[CH:13][CH:12]=1.C1CCCCC1>CN(C=O)C>[N:11]1[CH:16]=[CH:15][C:14]([CH2:17][N:7]2[C:6](=[O:8])[CH2:5][CH2:4][C:3]2=[O:9])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 8078CyclohexaneHCID 11439SuccinimideHCID 24758Sodium hydrideHCID 745704-(Chloromethyl)pyridinium chloride

Product 1

HCID 21695009HCID 21695009, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of sodium hydride (17.6 g, 0.44 mol) in DMF (500 mL) was stirred with ice bath cooling as succinimide (29.73 g, 0.3 mol) was cautiously added. 4-Picolyl chloride hydrochloride (32.81 g, 0.2 mol) was then added cautiously with vigorous stirring. The mixture was stirred at room temperature for 1 day and then at 100° C. for 2 days. The mixture was then cooled and filtered. The filtrate was concentrated in vacuo to give a black oil. This dark crude product was stirred four times with boiling cyclohexane (150 mL), each time decanting the boiling cyclohexane from the dark residue. Upon cooling the cyclohexane extracts, the desired product crystallized as colorless needles (23.05 g, 60.9%) which were filtered and air dried.

Workup

  1. additionwas cautiously added
  2. stirringThe mixture was stirred at room temperature for 1 day
  3. temperatureThe mixture was then cooled
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto give a black oil
  7. customeach time decanting the boiling cyclohexane from the dark residue
  8. temperatureUpon cooling the cyclohexane
  9. customthe desired product crystallized as colorless needles (23.05 g, 60.9%) which
  10. filtrationwere filtered
  11. customair dried

Sources & evidence

ORD record
ord-dcba331d0ef44082a6adca5b2a3f7f69
Source dataset
uspto-grants-1992_03
Patent number
US05098904

Reaction notes

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