Thionyl Chloride → 1-[3-(4-Chloromethylphenoxy)propyl]piperidine

HRID 657678Notes

Reaction equation

HRID 657678 reaction equation
O[CH2:2][C:3]1[CH:18]=[CH:17][C:6]([O:7][CH2:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:5][CH:4]=1.S(Cl)([Cl:21])=O>ClCCl>[Cl:21][CH2:2][C:3]1[CH:18]=[CH:17][C:6]([O:7][CH2:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 271606191-[3-(4-Hydroxymethylphenoxy)propyl]piperidine

Product 1

HCID 689095631-[3-(4-Chloromethylphenoxy)propyl]piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[3-(4-hydroxymethylphenoxy)propyl]piperidine (5.617 g) in dichloromethane (50 mL), cooled at a temperature close to 0° C., is added dropwise thionyl chloride (3 mL). The mixture is stirred for 18 hours at room temperature and concentrated under reduced pressure. The residue is crystallized in diethyl ether to give 1-[3-(4-chloromethylphenoxy)propyl]piperidine as an off white solid used without further purification.

Workup

  1. customclose to 0° C.
  2. concentrationconcentrated under reduced pressure
  3. customThe residue is crystallized in diethyl ether

Sources & evidence

ORD record
ord-b1981bcfd69f4ad38362ad12d8f6c1eb
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

Loading…