Thionyl Chloride → 1-{[3-(Chloromethyl)phenyl]methyl}piperidine hydrochloride

HRID 35603Notes

Reaction equation

HRID 35603 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[CH2:11]O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:18])=O>ClCCl>[ClH:18].[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[CH2:11][Cl:18])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 7164645(3-((Piperidin-1-yl)methyl)phenyl)methanol

Product 1

HCID 212945121-{[3-(Chloromethyl)phenyl]methyl}piperidine hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the above alcohol (2.05 g) in dry dichloromethane (60 ml) was treated with a solution of thionyl chloride (3.3 ml) in dry dichloromethane (10 ml) and heated under reflux for 2.5 hours. The product was evaporated in vacuo to produce an oil which was crystallised from dry tetrahydrofuran to give colourless crystals of 3-piperidinomethylbenzyl chloride hydrochloride (m.p. 156°-160° C.).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2.5 hours
  3. customThe product was evaporated in vacuo
  4. customto produce an oil which
  5. customwas crystallised from dry tetrahydrofuran

Sources & evidence

ORD record
ord-d1616e458ccd4cdc807717a4f709da66
Source dataset
uspto-grants-1988_08
Patent number
US04767769

Reaction notes

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