Potassium Iodide → HCID 21428904, compound

HRID 437662Notes

Reaction equation

HRID 437662 reaction equation
[Cl:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)=[O:6].[C:13]1([N:19]2[C:23]3([CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[C:22](=[O:29])[NH:21][CH2:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[I-].[K+]>CC(C)CC(=O)C>[OH2:6].[ClH:1].[ClH:1].[O:29]=[C:22]1[C:23]2([CH2:24][CH2:25][N:26]([CH2:2][CH2:3][NH:4][C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=3)=[O:6])[CH2:27][CH2:28]2)[N:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:20][NH:21]1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 705561-Phenyl-1,3,8-triazaspiro(4.5)decan-4-oneHCID 21428903HCID 21428903, compound

Product 1

HCID 21428904HCID 21428904, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 4.4 parts of N-(2-chloroethyl)-2-pyridinecarboxamide, 13.8 parts of 1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one, 3.3 parts of potassium iodide and 200 parts of 4-methyl-2-pentanone is stirred and refluxed for 24 hours. The reaction mixture is evaporated and the residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is converted into the hydrochloride salt in 2-propanol. The salt is filtered off and crystallized from ethanol, yielding 1.1 parts of N-[2-(4-oxo-1-phenyl-1,3,8-triazaspiro[4,5]dec-8-yl)ethyl]-2-pyridinecarboxamide dihydrochloride hydrate; mp. 250.5° C.

Workup

  1. temperaturerefluxed for 24 hours
  2. customThe reaction mixture is evaporated
  3. customthe residue is purified by column-chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  5. customThe pure fractions are collected
  6. customthe eluent is evaporated
  7. filtrationThe salt is filtered off
  8. customcrystallized from ethanol

Sources & evidence

ORD record
ord-219e6cd173e5461389feba78b0664820
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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