Potassium Iodide → Lorcainide Hydrochloride

HRID 26754Notes

Reaction equation

HRID 26754 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[C:9](=[O:17])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].Br[CH:33]([CH3:35])[CH3:34]>CC(=O)C.C(O)CCC>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH:18]2[CH2:23][CH2:22][N:21]([CH:33]([CH3:35])[CH3:34])[CH2:20][CH2:19]2)[C:9](=[O:17])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 63582-Bromopropane2×HCID 10340Sodium CarbonateHCID 162188N-(4-Chlorophenyl)-N-4-piperidinylbenzeneacetamide

Product 1

HCID 6917855Lorcainide Hydrochloride

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 2631-ButanolSolvent

Procedure

To a stirred suspension of 5 parts of N-(4-chlorophenyl)-N-(4-piperidinyl)benzeneacetamide, 5 parts of sodium carbonate, a few crystals of potassium iodide in 200 parts of butanol is added dropwise 4 parts of 2-bromopropane at room temperature. After the addition is complete, the whole is stirred and refluxed for 20 hours. Then the second portion of 4 parts of 2-bromopropane is added and stirring and refluxing is continued for another 19 hours. The reaction mixture is cooled, filtered and the filtrate is evaporated. From the oily free base, the hydrochloride salt is prepared in the conventional manner in 1,1'-oxybisethane and 2-propanone. The precipitated solid salt is filtered off and crystallized from a mixture of 2-propanone and 2-propanol, yielding 2 parts of N-(4-chlorophenyl)-N-[1-(1-methylethyl)-4-piperidinyl]benzeneacetamide hydrochloride; mp. 263° C.

Workup

  1. additionAfter the addition
  2. temperaturerefluxed for 20 hours
  3. stirringstirring
  4. temperaturerefluxing
  5. temperatureThe reaction mixture is cooled
  6. filtrationfiltered
  7. customthe filtrate is evaporated
  8. filtrationThe precipitated solid salt is filtered off
  9. customcrystallized from a mixture of 2-propanone and 2-propanol

Sources & evidence

ORD record
ord-2055fdd663aa4ba8a5f9123ffc73d573
Source dataset
uspto-grants-1979_04
Patent number
US04151286

Reaction notes

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