ChemicalBook--->CAS DataBase List--->586-60-7

586-60-7

586-60-7 Structure

586-60-7 Structure
IdentificationBack Directory
[Name]

DYCLONINE
[CAS]

586-60-7
[Synonyms]

dyclonin
yclonine
DYCLONINE
dyclocaine
Dyclonine HCI
DYCLONINE USP/EP/BP
4'-Butoxy-β-piperidinopropiophenone
4’-butoxy-3-piperidino-propiophenon
1-(4-butoxyphenyl)-3-(1-piperidinyl)-1-propanon
1-(4-butoxyphenyl)-3-(piperidin-1-yl)propan-1-one
1-Propanone, 1-(4-butoxyphenyl)-3-(1-piperidinyl)-
[EINECS(EC#)]

1312995-182-4
[Molecular Formula]

C18H27NO2
[MDL Number]

MFCD00242641
[MOL File]

586-60-7.mol
[Molecular Weight]

289.41
Questions And AnswerBack Directory
[Preparation]

DYCLONINE hydrochloride of pharmaceutical grade was synthesized from p-hydroxyacetophenone and bromobutane via a two-step reaction using a phase-transfer catalyst. First, the intermediate p-butoxyacetophenone was generated using a phase-transfer catalyst, and then reacted with piperidine hydrochloride and paraformaldehyde to produce the final product. The structure of the synthesized product was confirmed by 1H-NMR and MS. The results showed that the overall yield of the reaction exceeded 90%, and the process was simple, easy to operate, and suitable for industrial production.

Chemical PropertiesBack Directory
[Boiling point ]

424.5±25.0 °C(Predicted)
[density ]

1.017±0.06 g/cm3(Predicted)
[pka]

8.68±0.10(Predicted)
Hazard InformationBack Directory
[Originator]

Dyclone,Dow,US,1956
[Uses]

anesthetic (local)
[Definition]

ChEBI: N-Ethylpiperidine in which one of the hydrogens attached to the methyl group is substituted by a 4-butoxybenzoyl group.
[Manufacturing Process]

A mixture of 17.6 grams of p-n-butoxyacetophenone, 12.1 grams of piperidine hydrochloride, 4.5 grams paraformaldehyde, 0.25 cc concentrated hydrochloric acid, 52.5 cc nitroethane, 7.5 cc of 95% ethanol, and 15 cc of toluene was boiled under reflux for one hour, removing water formed in the reaction by means of a condensate trap. The mixture was then cooled. The crystals which formed were collected by filtration, washed with anhydrous ether and recrystallized from methyl ethyl ketone. The crystals thus obtained, which melted at 174-175°C, were shown by analysis to be 4-n-butoxy-β- piperidinopropiophenone hydrochloride.
[Brand name]

Dyclone (AstraZeneca).
[Therapeutic Function]

Local anesthetic
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