Dimethylformamide → 1-(2-Chloroethyl)-4-(4-fluorobenzoyl)piperidine hydrochloride

HRID 2458

Reaction equation

HRID 2458 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15]O)[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.CN(C=O)C.S(Cl)([Cl:26])=O>C(Cl)Cl>[ClH:26].[Cl:26][CH2:15][CH2:14][N:11]1[CH2:12][CH2:13][CH:8]([C:6](=[O:7])[C:5]2[CH:17]=[CH:18][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 148921654-(4-Fluorobenzoyl)-1-(2-hydroxyethyl)piperidine

Product 1

HCID 675753381-(2-Chloroethyl)-4-(4-fluorobenzoyl)piperidine hydrochlorideYield 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In an atmosphere of dry air, 4-(4-fluorobenzoyl)-1-(2-hydroxyethyl)piperidine (1.96 g, 7.8 mmol) was dissolved in methylene chloride (10 ml) to which, with cooling in an ice bath, were subsequently added dropwise DMF (0.1 ml) and thionyl chloride (2.5 ml, 34.2 mmol). After 7 hours of stirring at room temperature, the solvent was removed by evaporation, and the resulting residue was subjected to azeotropic distillation using benzene (15 ml×2). Thereafter, the thus obtained residue was washed with an ether-methylene chloride (4:1) mixture solution (30 ml) to obtain 2.3 g (96.3%) of the title compound in the form of light beige powder.

Workup

  1. temperaturewith cooling in an ice bath
  2. customthe solvent was removed by evaporation
  3. distillationthe resulting residue was subjected to azeotropic distillation
  4. washThereafter, the thus obtained residue was washed with an ether-methylene chloride (4:1) mixture solution (30 ml)

Sources & evidence

ORD record
ord-761b0c03342a44cd91f901367699772b
Source dataset
uspto-grants-1998_03
Patent number
US05728835

Linked notes

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