Thionyl Chloride → 4-(Chloromethyl)piperidine--hydrogen chloride (1/1)

HRID 1389240Notes

Reaction equation

HRID 1389240 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1>C(Cl)(Cl)Cl>[ClH:3].[Cl:3][CH2:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 4207714-Piperidinemethanol

Product 1

HCID 124281464-(Chloromethyl)piperidine--hydrogen chloride (1/1)Yield 88%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 58 ml of thionyl chloride in 250 ml of chloroform, there is added dropwise a solution of 45 g (0.39 mole) of 4-hydroxymethylpiperidine in 200 ml of chloroform. After stirring for 1 hour under reflux, the reaction mixture is evaporated in a vacuum and the residue is triturated with diethyl ether. There are obtained 54.2 g of 4-chloromethylpiperidine hydrochloride (88% of theory); m.p. 130°-132° C.

Workup

  1. temperatureunder reflux
  2. customthe reaction mixture is evaporated in a vacuum
  3. customthe residue is triturated with diethyl ether

Sources & evidence

ORD record
ord-acad6d782b82423a9fb510d54fae73e3
Source dataset
uspto-grants-1981_01
Patent number
US04243807

Reaction notes

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