Potassium thiocyanate → HCID 21490103, compound

HRID 1973632Notes

Reaction equation

HRID 1973632 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH:10]([CH3:11])[CH2:9][CH2:8][CH2:7][CH:6]1[CH3:12])=[O:4].[S-:13][C:14]#[N:15].[K+]>C(O)C>[S:13]([CH2:2][C:3]([N:5]1[CH:10]([CH3:11])[CH2:9][CH2:8][CH2:7][CH:6]1[CH3:12])=[O:4])[C:14]#[N:15]

Participants

4

Reactant 2

HCID 516872Potassium thiocyanateHCID 44631492-chloro-1-(2,6-dimethylpiperidin-1-yl)ethanone

Product 1

HCID 21490103HCID 21490103, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(α-Chloroacetyl)-2,6-dimethylpiperidine (18.9 grams; 0.1 mol), potassium thiocyanate (18 grams; 0.2 mol) and ethanol (100 ml) were charged into a glass reaction flask equipped with a mechanical stirrier and reflux condenser. The reaction mixture was heated at reflux, with stirring, for a period of about 3 hours. After this time the reaction mixture was cooled and filtered. The ethanol was evaporated under reduced pressure to yield a dark solid. The solid was extracted with two 200 ml portions of hot benzene. The benzene extracts were combined, were filtered and treated with activated charcoal. The benzene solution was then evaporated under reduced pressure to yield a dark colored oil which solidified upon standing. The solidified product then crystallized, to yield 1-(α-thiocyanoacetyl)-2,6-dimethylpiperidine as a pale yellow solid having a melting point of 81° to 82° C. and leaving the following elemental analysis as calculated for C10H16N2OS.

Workup

  1. customequipped with a mechanical stirrier
  2. temperaturereflux condenser
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux
  5. temperatureAfter this time the reaction mixture was cooled
  6. filtrationfiltered
  7. customThe ethanol was evaporated under reduced pressure
  8. customto yield a dark solid
  9. extractionThe solid was extracted with two 200 ml portions of hot benzene
  10. filtrationwere filtered
  11. additiontreated with activated charcoal
  12. customThe benzene solution was then evaporated under reduced pressure
  13. customto yield a dark colored oil which
  14. customThe solidified product then crystallized

Sources & evidence

ORD record
ord-2824643dfe994897a0fb1673d0f4a9d1
Source dataset
uspto-grants-1976_12
Patent number
US03998808

Reaction notes

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