Thionyl Chloride → 1-(2-(4-(Chloromethyl)phenoxy)ethyl)piperidine hydrochloride

HRID 1066430Notes

Reaction equation

HRID 1066430 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:17]=[CH:16][C:13]([CH2:14]O)=[CH:12][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:20])=O>C(Cl)CCl>[ClH:20].[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:17]=[CH:16][C:13]([CH2:14][Cl:20])=[CH:12][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 9816107[4-(2-Piperidin-1-ylethoxy)phenyl]methanol

Product 1

HCID 98607851-(2-(4-(Chloromethyl)phenoxy)ethyl)piperidine hydrochloride

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The solution of 4-(2-piperidinylethoxy)benzyl alcohol in ethylene dichloride can be combined with thionyl chloride and heated until the reaction is complete. Upon cooling, the mixture can be concentrated, followed by addition of 1,2-dimethoxyethane and additional concentration. The precipitate can be collected and dried to yield intermediate 4-(2-piperidinylethoxy)benzylchloride hydrochloride, as shown in Scheme IX.

Workup

  1. temperatureheated until the reaction
  2. temperatureUpon cooling
  3. concentrationthe mixture can be concentrated
  4. additionfollowed by addition of 1,2-dimethoxyethane and additional concentration
  5. customThe precipitate can be collected
  6. customdried

Sources & evidence

ORD record
ord-a3b98e294c0b43fb85b9ab899821648e
Source dataset
uspto-grants-2001_06
Patent number
US06242605B1

Reaction notes

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