Potassium Iodide → Ethyl 4-[5-(4-fluorophenyl)-5-(3-pyridinyl)pentyl]2-methyl-1-piperazinecarboxylate

HRID 1494632Notes

Reaction equation

HRID 1494632 reaction equation
Cl[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.[N:20]1([C:26]([O-:28])=[O:27])[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.[CH2:29](N(CC)CC)[CH3:30].[I-].[K+].[CH3:38]N(C)C=O>>[F:13][C:10]1[CH:11]=[CH:12][C:7]([CH:6]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH2:5][CH2:4][CH2:3][CH2:2][N:23]2[CH2:24][CH2:25][N:20]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:21]([CH3:38])[CH2:22]2)=[CH:8][CH:9]=1

Participants

6

Reactant 5

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 8471TriethylamineHCID 147225623-[5-Chloro-1-(4-fluorophenyl)pentyl]pyridineHCID 21904562Piperazine-1-carboxylate

Product 1

HCID 15167760Ethyl 4-[5-(4-fluorophenyl)-5-(3-pyridinyl)pentyl]2-methyl-1-piperazinecarboxylateYield 96.7%

Conditions

Temperature
70 °C

Procedure

A mixture of 14 parts of 3-[5-chloro-1-(4-fluorophenyl)pentyl]pyridine, 7.75 parts of ethyl 2-methyl-1-(piperazinecarboxylate, 8.7 parts of N,N-diethylethanamine, 0.1 parts of potassium iodide and 198 parts of N,N-dimethylformamide was stirred for 40 hours at 70° C. The reaction mixture was evaporated and the residue was taken up in a mixture of water and sodium carbonate. The aqueous layer was extracted with trichloromethane. The extract was washed with a sodium carbonate solution in water and water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 18 parts (96.7%) of ethyl 4-[5-(4-fluorophenyl)-5-(3-pyridinyl)pentyl]-2-methyl-1-piperazinecarboxylate as a residue (int. 38).

Workup

  1. customThe reaction mixture was evaporated
  2. additionthe residue was taken up in a mixture of water and sodium carbonate
  3. extractionThe aqueous layer was extracted with trichloromethane
  4. washThe extract was washed with a sodium carbonate solution in water and water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated

Sources & evidence

ORD record
ord-3b6f5df1da1e4df2954865d9ec9b1ba6
Source dataset
uspto-grants-1991_06
Patent number
US05026853

Reaction notes

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