Ethanol → HCID 14230185, compound

HRID 35342Notes

Reaction equation

HRID 35342 reaction equation
S1C=CC=C1.C(O)C.[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([C:43]2[CH:48]=[CH:47][C:46]([F:49])=[CH:45][CH:44]=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]([CH2:41][OH:42])[CH2:21]2)=[CH:12][CH:11]=1.[H][H]>[Pt].CO>[NH2:37][C:33]1[CH:32]=[C:31]([CH3:40])[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:43]3[CH:48]=[CH:47][C:46]([F:49])=[CH:45][CH:44]=3)[CH2:21][CH:22]2[CH2:41][OH:42])=[C:35]([CH3:36])[CH:34]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 8030ThiopheneHCID 142301694-[4,4-bis(4-fluorophenyl)butyl]-N-(2,6-dimethyl-4-nitrophenyl)-2-(hydroxymethyl)-1-piperazineacetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 14230185HCID 14230185, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

To 1 part of a solution of 2 parts of thiophene in 40 parts of ethanol were added 3.4 parts of 4-[4,4-bis(4-fluorophenyl)butyl]-N-(2,6-dimethyl-4-nitrophenyl)-2-(hydroxymethyl)-1-piperazineacetamide and 120 parts of methanol. The whole is hydrogenated at normal pressure and at room temperature with 2 parts of platinum-on-charcoal catalyst 5%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The oily residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The oily residue solidified on cooling in a 2-propanone/CO2 -bath. The product was dried, yielding 1.73 parts (54%) of N-(4-amino-2,6-dimethylphenyl)-4-[4,4-bis(4-fluorophenyl)butyl]-2-(hydroxymethyl)-1-piperazineacetamide; mp. 85.2° C. (compound 156).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe oily residue was purified by column-chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated
  7. temperatureon cooling in a 2-propanone/CO2
  8. customThe product was dried

Sources & evidence

ORD record
ord-9498fdaa68714d609561537cc6f6c9c9
Source dataset
uspto-grants-1988_08
Patent number
US04766125

Reaction notes

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