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

HRID 2185823Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2185823
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][NH:15][CH:14]([C:18]([NH:20][CH3:21])=[O:19])[CH2:13]2)=[CH:4][CH:3]=1.Cl[CH2:30][C:31]([NH:33][C:34]1[C:39]([CH3:40])=[CH:38][C:37]([CH3:41])=[CH:36][C:35]=1[CH3:42])=[O:32].C(=O)([O-])[O-].[Na+].[Na+]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)[CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][N:15]([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])[CH:14]([C:18]([NH:20][CH3:21])=[O:19])[CH2:13]2)=[CH:4][CH:3]=1

Komponenten

4

Edukt 3

HCID 10340Sodium CarbonateHCID 23056352-chloro-N-(2,4,6-trimethylphenyl)acetamideHCID 224525354-[4,4-bis(4-fluorophenyl)butyl]-N-methyl-2-piperazine-carboxamide

Produkt 1

HCID 142301324-[4,4-bis(4-fluorophenyl)butyl]-2-[(methylamino)carbonyl]-N-(2,4,6-trimethylphenyl)-1-piperazineacetamideAusbeute 51,5 %

Versuchsvorschrift

A mixture of 5.8 g of 4-[4,4-bis(4-fluorophenyl)butyl]-N-methyl-2-piperazine-carboxamide, 3.6 g of 2-chloro-N-(2,4,6-trimethylphenyl)acetamide, 2.12 g of sodium carbonate and 150 ml of MIK is stirred and refluxed for 18 hours. The reaction mixture is cooled and washed with water. The organic phase is 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 4.34 g of 4-[4,4-bis(4-fluorophenyl)butyl]-2-[(methylamino)carbonyl]-N-(2,4,6-trimethylphenyl)-1-piperazineacetamide (compound 2, mp. 90.2° C.).

Aufarbeitung

  1. temperaturerefluxed for 18 hours
  2. temperatureThe reaction mixture is cooled
  3. washwashed with water
  4. customThe organic phase is dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by column-chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  9. customThe pure fractions are collected
  10. customthe eluent is evaporated
  11. customThe residue is dried

Quellen und Nachweise

ORD-Eintrag
ord-d36dcc88ba1d44d0a90181498b0a07a5
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06403589B1

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