Thionyl Chloride → 3-[4-(Pyridin-3-ylmethyl)phenyl]propyl chloride hydrochloride

HRID 569147Notes

Reaction equation

HRID 569147 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16]O)=[CH:10][CH:9]=2)[CH:2]=1.S(Cl)([Cl:20])=O>C(Cl)Cl>[ClH:20].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][Cl:20])=[CH:10][CH:9]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 138227803-[4-(Pyridin-3-ylmethyl)phenyl]propanol

Product 1

HCID 201486293-[4-(Pyridin-3-ylmethyl)phenyl]propyl chloride hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 10 ml of methylene chloride was dissolved 500 mg of 3-[4-(pyridin-3-ylmethyl)phenyl]propanol, and 0.80 ml of thionyl chloride was added to the resulting solution with ice-cooling, after which the resulting mixture was subjected to reaction under reflux for one hour. The solvent and the excessive thionyl chloride were removed by distillation under reduced pressure, to obtain 3-[4-(pyridin-3-ylmethyl)phenyl]propyl chloride hydrochloride as the residue. This residue was dissolved in 4 ml of dimethyl sulfoxide.

Workup

  1. additionwas added to the resulting solution with ice-
  2. temperaturecooling
  3. customafter which the resulting mixture was subjected to reaction
  4. temperatureunder reflux for one hour
  5. customThe solvent and the excessive thionyl chloride were removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-131ad0a0f264411b8e8823a242f77a01
Source dataset
uspto-grants-1988_03
Patent number
US04731370

Reaction notes

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