Ethanol → HCID 14230140, compound

HRID 35343Notes

Reaction equation

HRID 35343 reaction equation
S1C=CC=C1.C(O)C.[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([C:45]2[CH:50]=[CH:49][C:48]([F:51])=[CH:47][CH:46]=2)[CH2:17][CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][N:23]([CH2:26][C:27]([NH:29][C:30]3[C:35]([CH3:36])=[CH:34][C:33]([N+:37]([O-])=O)=[CH:32][C:31]=3[CH3:40])=[O:28])[CH:22]([C:41]([NH:43][CH3:44])=[O:42])[CH2:21]2)=[CH:12][CH:11]=1.[H][H]>[Pd].CO>[NH2:37][C:33]1[CH:34]=[C:35]([CH3:36])[C:30]([NH:29][C:27](=[O:28])[CH2:26][N:23]2[CH2:24][CH2:25][N:20]([CH2:19][CH2:18][CH2:17][CH:16]([C:13]3[CH:12]=[CH:11][C:10]([F:9])=[CH:15][CH:14]=3)[C:45]3[CH:46]=[CH:47][C:48]([F:51])=[CH:49][CH:50]=3)[CH2:21][CH:22]2[C:41]([NH:43][CH3:44])=[O:42])=[C:31]([CH3:40])[CH:32]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 8030ThiopheneHCID 14230129HCID 14230129, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14230140HCID 14230140, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 1 part of a solution of 2 parts of thiophene in 40 parts of ethanol were added 3 parts of 4-[4,4-bis(4-fluorophenyl)butyl]-N-(2,6-dimethyl-4-nitrophenyl)-2-[(methylamino)carbonyl]-1-piperazineacetamide and 120 parts of methanol. The whole was hydrogenated at normal pressure and at room temperature with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was suspended in 2,2'-oxybispropane, yielding 2.14 parts of N-(4-amino-2,6-dimethylphenyl)-4-[4,4-bis(4-fluorophenyl)butyl]-2-[(methylamino)carbonyl]-1-piperazineacetamide; mp. 111.7° C. (compound 162).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column-chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated

Sources & evidence

ORD record
ord-1c2097d3c9d14e7e83bd302cd874adad
Source dataset
uspto-grants-1988_08
Patent number
US04766125

Reaction notes

Loading…