Thionyl Chloride → HCID 12769347, compound

HRID 1732570Notes

Reaction equation

Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][C:18]=1[Cl:19])[CH2:6][N:7]1[CH2:12][CH2:11][CH:10]=[C:9]([C:13]([OH:15])=[O:14])[CH2:8]1.S(Cl)(Cl)=O>>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][C:18]=1[Cl:19])[CH2:6][N:7]1[CH2:12][CH2:11][CH:10]=[C:9]([C:13]([O:15][CH2:4][CH2:3][CH2:18][CH3:17])=[O:14])[CH2:8]1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 12769345HCID 12769345, compound

Product 1

HCID 12769347HCID 12769347, compoundYield 102.2%

Conditions

Temperature: 25 °C

Procedure

A mixture of 1-(3,4-dichlorobenzyl)-1,2,5,6-tetrahydropyridine-3-carboxylic acid hydrochloride (2.0 g.) and thionyl chloride (15 ml.) was heated under reflux for 30 minutes. Excess thionyl chloride was removed by evaporation and the residue was mixed with toluene and then evaporated. n-Butyl alcohol (30 ml.) was added to the cooled residual solid and the mixture was stirred at 25° C. for 1 hour, during which time all the solid dissolved. The solution obtained was heated under reflux for 10 minutes and then excess n-butyl alcohol was removed by evaporation. The residue was recrystallised from acetone/ether to give n-butyl 1-(3,4-dichlorobenzyl)-1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride (1.2 g.), m.p. 160°-162° C.

Workup

temperaturewas heated
temperatureunder reflux for 30 minutes
customExcess thionyl chloride was removed by evaporation
additionthe residue was mixed with toluene
customevaporated
additionn-Butyl alcohol (30 ml.) was added to the cooled residual solid
dissolutiondissolved
customThe solution obtained
temperaturewas heated
temperatureunder reflux for 10 minutes
customexcess n-butyl alcohol was removed by evaporation
customThe residue was recrystallised from acetone/ether

Sources & evidence

ORD record: ord-c3e73824504949f49c9bccdd92bfaaa6
Source dataset: uspto-grants-1980_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04238488

Reaction notes

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