Sodium Carbonate → 4-[4,4-bis(4-fluorophenyl)butyl]-3-[(methylamino)-carbonyl]-N-(2,4,6-trimethylphenyl)-1-piperazineacetamide

HRID 2185822Notes

Reaction equation

HRID 2185822 reaction equation
I[CH2:2][CH2:3][CH2:4][CH:5]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1.[CH3:20][NH:21][C:22]([CH:24]1[NH:29][CH2:28][CH2:27][N:26]([CH2:30][C:31]([NH:33][C:34]2[C:39]([CH3:40])=[CH:38][C:37]([CH3:41])=[CH:36][C:35]=2[CH3:42])=[O:32])[CH2:25]1)=[O:23].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[F:12][C:9]1[CH:10]=[CH:11][C:6]([CH:5]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH2:4][CH2:3][CH2:2][N:29]2[CH2:28][CH2:27][N:26]([CH2:30][C:31]([NH:33][C:34]3[C:39]([CH3:40])=[CH:38][C:37]([CH3:41])=[CH:36][C:35]=3[CH3:42])=[O:32])[CH2:25][CH:24]2[C:22]([NH:21][CH3:20])=[O:23])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 1039681,1'-(4-Iodobutylidene)bis[4-fluorobenzene]HCID 142302353-[(methylamino)carbonyl]-N-(2,4,6-trimethylphenyl)-1-piperazineacetamide

Product 1

HCID 142300824-[4,4-bis(4-fluorophenyl)butyl]-3-[(methylamino)-carbonyl]-N-(2,4,6-trimethylphenyl)-1-piperazineacetamideYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 6.7 g of 1,1′-(4-iodobutylidene)bis[4-fluorobenzene], 5.2 g of 3-[(methylamino)carbonyl]-N-(2,4,6-trimethylphenyl)-1-piperazineacetamide, 2.3 g sodium carbonate and 38 ml DMF is stirred for 18 hours at 70° C. The reaction mixture is cooled and poured onto ice-water. The product is extracted with DCM. The extract is washed with water, dried, filtered and 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 dried, yielding 4.23 g of 4-[4,4-bis(4-fluorophenyl)butyl]-3-[(methylamino)-carbonyl]-N-(2,4,6-trimethylphenyl)-1-piperazineacetamide (compound 1, mp. 82.3° C.).

Workup

  1. temperatureThe reaction mixture is cooled
  2. additionpoured onto ice-water
  3. extractionThe product is extracted with DCM
  4. washThe extract is 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 (95:5 by volume) as eluent
  10. customThe pure fractions are collected
  11. customthe eluent is evaporated
  12. customThe residue is dried

Sources & evidence

ORD record
ord-2a9e7fa9d2b74b178549c9d01854638d
Source dataset
uspto-grants-2002_06
Patent number
US06403589B1

Reaction notes

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