Chloroform → (4-(Chloromethyl)piperidin-1-yl)(phenyl)methanone

HRID 1389237Notes

Reaction equation

HRID 1389237 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][CH:12]([CH2:15]O)[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:19])=O.C(Cl)(Cl)Cl>O>[C:1]([N:9]1[CH2:14][CH2:13][CH:12]([CH2:15][Cl:19])[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 24386Thionyl ChlorideHCID 102628704-Piperidinemethanol, 1-benzoyl-

Product 1

HCID 11118098(4-(Chloromethyl)piperidin-1-yl)(phenyl)methanoneYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Hydroxymethylpyridine is hydrogenated in methanol at 140° C. under 200 atmospheres of hydrogen pressure in the presence of ruthenium oxide, producing 4-hydroxymethylpiperidine, b.p. 126°-130° C./14 mm Hg; m.p. 55°-56° C. Reaction with benzoyl chloride produces N-benzoyl-4-hydroxymethylpiperidine (m.p. 83°-85° C.). A mixture of 135.0 g of N-benzoyl-4-hydroxymethyl-piperidine, 90 ml of thionyl chloride and 900 ml of chloroform is heated under reflux for 4 hours. Thereafter, the reaction mixture is mixed with water, while cooling with ice, and the organic phase is washed neutral with an aqueous solution of sodium bicarbonate, dried over anhydrous sodium sulfate and evaporated. There are obtained 132.0 g (90% of theory) of N-benzoyl-4-chloromethylpiperidine; m.p. 68°-70° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 4 hours
  3. temperaturewhile cooling with ice
  4. washthe organic phase is washed neutral with an aqueous solution of sodium bicarbonate
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-cbd117ac463e4036ad51d756e0d4f69a
Source dataset
uspto-grants-1981_01
Patent number
US04243807

Reaction notes

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