Potassium Iodide → N-[4-(aminocarbonyl)-2,6-dichlorophenyl]-4-[5-(4-fluorophenyl)-5-(3-pyridinyl)pentyl]-1-piperazineacetamide trihydrochloride

HRID 1494653Notes

Reaction equation

HRID 1494653 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1.NC([CH:23]1[NH:28][CH2:27][CH2:26][N:25]([CH2:29][C:30]([NH:32][C:33]2[C:38]([Cl:39])=[CH:37][C:36]([C:40]([NH2:42])=[O:41])=[CH:35][C:34]=2[Cl:43])=[O:31])[CH2:24]1)=O.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CN(C)C(=O)C>[ClH:1].[ClH:39].[ClH:1].[NH2:42][C:40]([C:36]1[CH:35]=[C:34]([Cl:43])[C:33]([NH:32][C:30](=[O:31])[CH2:29][N:25]2[CH2:24][CH2:23][N:28]([CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([C:7]3[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=3)[C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[CH2:27][CH2:26]2)=[C:38]([Cl:39])[CH:37]=1)=[O:41]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 147225393-(aminocarbonyl)-N-[4-(aminocarbonyl)-2,6-dichlorophenyl]-1-piperazineacetamideHCID 147225623-[5-Chloro-1-(4-fluorophenyl)pentyl]pyridine

Product 1

HCID 86744878N-[4-(aminocarbonyl)-2,6-dichlorophenyl]-4-[5-(4-fluorophenyl)-5-(3-pyridinyl)pentyl]-1-piperazineacetamide trihydrochloride

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4.72 parts of 3-[5-chloro-1-(4-fluorophenyl)pentyl]pyridine, 5.62 parts of 3-(aminocarbonyl)-N-[4-(aminocarbonyl)-2,6-dichlorophenyl]-1-piperazineacetamide, 1.58 parts of sodium carbonate, 0.1 parts of potassium iodide and 90 parts of N,N-dimethylacetamide was stirred for 48 hours at ±90° C. After evaporation, the residue was taken up in water and the product was extracted twice with dichlormethane. The combined extracts were washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (93:7 by volume) as eluent. The first fraction was collected and the eluent was evaporated. The residue was converted into the hydrochloride salt in 2-propanol. The salt was filtered off and dried, yielding 2.3 parts (20.9%) of 3-aminocarbonyl)-N-[4-(aminocarbonyl)-2,6-dichlorophenyl]-4-[5-(4-fluorophenyl)-5-(3-pyridinyl)pentyl]-1-piperazineacetamide trihydrochloride, dihydrate; mp. 173.0° C. (compound 43).

Workup

  1. customAfter evaporation
  2. extractionthe product was extracted twice with dichlormethane
  3. washThe combined extracts were washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol
  9. customThe first fraction was collected
  10. customthe eluent was evaporated
  11. filtrationThe salt was filtered off
  12. customdried

Sources & evidence

ORD record
ord-61554b26b79b49b8a8850a6f9bdacbdc
Source dataset
uspto-grants-1991_06
Patent number
US05026853

Reaction notes

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