Thionyl Chloride → HCID 19085476, compound

HRID 962467Notes

Reaction equation

HRID 962467 reaction equation
S(Cl)([Cl:3])=O.[O:5]([CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][CH2:17][CH:16]([CH2:20]O)[CH2:15]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(Cl)(Cl)Cl>[ClH:3].[Cl:3][CH2:20][CH:16]1[CH2:17][CH2:18][CH2:19][N:14]([CH2:13][CH2:12][O:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:15]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 19085450HCID 19085450, compound

Product 1

HCID 19085476HCID 19085476, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of thionyl chloride (1.7 ml) in chloroform (10 ml) was added dropwise with stirring to a solution of 1-(2-phenoxyethyl)piperidin-3-ylmethanol (5.0 g) in chloroform (70 ml) at 0°-5° C. After the addition the mixture was boiled under reflux for 2.5 hours. The solvent was removed under reduced pressure and the residue was triturated with ether and filtered to give 3-chloromethyl-1-(2-phenoxyethyl)piperidine hydrochloride, m.p. 125°-127° C.

Workup

  1. additionAfter the addition the mixture
  2. temperatureunder reflux for 2.5 hours
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was triturated with ether
  5. filtrationfiltered

Sources & evidence

ORD record
ord-a084506717944a73a31a93ab7fcbe613
Source dataset
uspto-grants-1998_06
Patent number
US05760035

Reaction notes

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