Potassium Iodide → HCID 20360356, compound

HRID 2082679Notes

Reaction equation

HRID 2082679 reaction equation
Cl.Cl[CH2:3][CH2:4][NH:5][CH:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2([OH:32])[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2([OH:32])[CH2:27][CH2:28][N:29]([CH2:3][CH2:4][NH:5][CH:6]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:30][CH2:31]2)=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 20360374HCID 20360374, compound

Product 1

HCID 20360356HCID 20360356, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 10 parts of N-(2-chloroethyl)-α-phenylbenzenemethanamine hydrochloride 7 parts of 4-(4-chlorophenyl)-4-piperidinol, 10.6 parts of sodium carbonate, 0.1 parts of potassium iodide and 80 parts of 4-methyl-2-pentanone is stirred and refluxed overnight. The reaction mixture is taken up in water and the layers are separated. The aqueous phase is extracted with 4-methyl--pentanone. The combined organic phases are washed with water, dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (96:4 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from a mixture of methylbenzene and 2,2'-oxybispropane. The product is filtered off and dried, yielding 4.5 parts of 4-(4-chlorophenyl)-1-{2-[(diphenylmethyl)amino]ethyl}-4-piperidinol; mp. 113.9° C.

Workup

  1. temperaturerefluxed overnight
  2. customthe layers are separated
  3. extractionThe aqueous phase is extracted with 4-methyl--pentanone
  4. washThe combined organic phases are washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is purified by column-chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol (96:4 by volume) as eluent
  10. customThe pure fractions are collected
  11. customthe eluent is evaporated
  12. customThe residue is crystallized from a mixture of methylbenzene and 2,2'-oxybispropane
  13. filtrationThe product is filtered off
  14. customdried

Sources & evidence

ORD record
ord-a9a6c932ab984e4883eb8ee48cae4bb4
Source dataset
uspto-grants-1978_04
Patent number
US04082755

Reaction notes

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