Ethanol → HCID 21490097, compound

HRID 1973633Notes

Reaction equation

HRID 1973633 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH:10]([CH3:11])[CH2:9][CH:8]([CH3:12])[CH2:7][CH:6]1[CH3:13])=[O:4].[S-:14][C:15]#[N:16].[K+].[I-].[Na+].C(O)C>C1C=CC=CC=1>[S:14]([CH2:2][C:3]([N:5]1[CH:10]([CH3:11])[CH2:9][CH:8]([CH3:12])[CH2:7][CH:6]1[CH3:13])=[O:4])[C:15]#[N:16]

Participants

6

Reactant 4

HCID 702EthanolHCID 5238Sodium IodideHCID 516872Potassium thiocyanateHCID 214900802-Chloro-1-(2,4,6-trimethyl-1-piperidinyl)ethanone

Product 1

HCID 21490097HCID 21490097, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1-(α-Chloroacetyl)-2,4,6-trimethylpiperidine (18 grams; 0.9 mol), potassium thiocyanate (18 grams; 0.2 mol), sodium iodide (a few crystals) and ethanol (100 ml) were charged into a glass reaction flask equipped with a mechanical stirrer and reflux condenser. The reaction mixture was heated at reflux for a period of about 3 hours. After this time the mixture was cooled and filtered. The filtrate was evaporated leaving a solid product. The solid was then extracted with two 150 ml portions of hot benzene. The extracts were combined and evaporated under reduced pressure to yield an oil. This oil was refined by chromatography using Fuller's earth as an adsorbent and benzene as the elluent. The first 1000 ml of eluent were collected from the column and were stripped of benzene to yield 1-(α-thiocyanoacetyl)-2,4,6-trimethylpiperidine as a yellow oil having a refractive index of 1.5183 at 25° C. and having the following elemental analysis as calculated for C11H18N2OS.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturereflux condenser
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for a period of about 3 hours
  5. temperatureAfter this time the mixture was cooled
  6. filtrationfiltered
  7. customThe filtrate was evaporated
  8. customleaving a solid product
  9. extractionThe solid was then extracted with two 150 ml portions of hot benzene
  10. customevaporated under reduced pressure
  11. customto yield an oil
  12. customThe first 1000 ml of eluent were collected from the column

Sources & evidence

ORD record
ord-086179aea5304d98a68949e8f23869bb
Source dataset
uspto-grants-1976_12
Patent number
US03998808

Reaction notes

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