Potassium Iodide → N-{2-[1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4,5]dec-8-yl] ethyl}-1-methyl-1H-pyrrole-2-carboxamide hydrochloride

HRID 437663Notes

Reaction equation

HRID 437663 reaction equation
[Cl:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[N:8]([CH3:12])[CH:9]=[CH:10][CH:11]=1)=[O:6].[F:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:24]3([CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[C:23](=[O:30])[NH:22][CH2:21]2)=[CH:16][CH:15]=1.C(=O)([O-])O.[Na+].[I-].[K+]>CC(C)CC(=O)C>[ClH:1].[F:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:24]3([CH2:25][CH2:26][N:27]([CH2:2][CH2:3][NH:4][C:5]([C:7]4[N:8]([CH3:12])[CH:9]=[CH:10][CH:11]=4)=[O:6])[CH2:28][CH2:29]3)[C:23](=[O:30])[NH:22][CH2:21]2)=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 939151-(4-Fluorophenyl)-1,3,8-triazaspiro(4.5)decan-4-oneHCID 516892Sodium BicarbonateHCID 21428944N-(2-chloroethyl)-1-methyl-1H-pyrrole-2-carboxamide

Product 1

HCID 68118485N-{2-[1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4,5]dec-8-yl] ethyl}-1-methyl-1H-pyrrole-2-carboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 3.75 parts of N-(2-chloroethyl)-1-methyl-1H-pyrrole-2-carboxamide, 5 parts of 1-(4-fluorophenyl)-1,3,8-triazaspiro[4,5]decan-4-one, 1.7 parts of sodium hydrogen carbonate, 0.1 parts of potassium iodide and 160 parts of 4-methyl-2-pentanone is stirred and refluxed for 48 hours. The reaction mixture is cooled and the solvent is evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 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 and 2,2'-oxybispropane. The salt is filtered off and crystallized from methanol, yielding 0.8 parts of N-{2-[1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4,5]dec-8-yl] ethyl} -1-methyl-1H-pyrrole-2-carboxamide hydrochloride; mp. 273.4° C.

Workup

  1. temperaturerefluxed for 48 hours
  2. temperatureThe reaction mixture is cooled
  3. customthe solvent is evaporated
  4. customThe residue is purified by column-chromatography over silica gel using
  5. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  6. customThe pure fractions are collected
  7. customthe eluent is evaporated
  8. filtrationThe salt is filtered off
  9. customcrystallized from methanol

Sources & evidence

ORD record
ord-c1348b2e1ee04e47ae2e36bdcb9ca14b
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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