Thionyl Chloride → [4-(Chloromethyl)phenyl](piperidin-1-yl)methanone

HRID 1957181Notes

Reaction equation

HRID 1957181 reaction equation
O[CH2:2][C:3]1[CH:16]=[CH:15][C:6]([C:7]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1.S(Cl)([Cl:19])=O>C(Cl)(Cl)Cl>[Cl:19][CH2:2][C:3]1[CH:16]=[CH:15][C:6]([C:7]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 11644226[4-(Piperidine-1-carbonyl)phenyl]methanol

Product 1

HCID 16637309[4-(Chloromethyl)phenyl](piperidin-1-yl)methanoneYield 92%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The alcohol (6.97 mmol) of the preceding paragraph was dissolved in 15 mL CHCl3, followed by the addition of 0.66 mL thionyl chloride. The solution was refluxed for 1 hour and then allowed to stand at room temperature overnight. The volume was then reduced by 50% on a rotary evaporator and the solution was diluted with CCl4 and petroleum ether to induce crystallization. The product 1-(4'-chloromethylbenzoyl)piperidine was isolated in 92% yield and had a melting point of 106°-108° C.

Workup

  1. temperatureThe solution was refluxed for 1 hour
  2. customThe volume was then reduced by 50% on a rotary evaporator
  3. additionthe solution was diluted with CCl4 and petroleum ether
  4. customcrystallization

Sources & evidence

ORD record
ord-49cfd154d3824878a2f3ae8a0fbd215b
Source dataset
uspto-grants-1998_07
Patent number
US05783587

Reaction notes

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