Dimethylformamide → 4-[4,4-Bis(4-fluorophenyl)butyl]-2-(methoxymethyl)-1-(trifluoroacetyl)piperazine

HRID 35321Notes

Reaction equation

HRID 35321 reaction equation
[CH3:1][O:2][CH2:3][CH:4]1[CH2:9][NH:8][CH2:7][CH2:6][N:5]1[C:10](=[O:15])[C:11]([F:14])([F:13])[F:12].CN(C)C=O.I[CH2:22][CH2:23][CH2:24][CH:25]([C:33]1[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=1)[C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1>O>[F:32][C:29]1[CH:28]=[CH:27][C:26]([CH:25]([C:33]2[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=2)[CH2:24][CH2:23][CH2:22][N:8]2[CH2:7][CH2:6][N:5]([C:10](=[O:15])[C:11]([F:14])([F:13])[F:12])[CH:4]([CH2:3][O:2][CH3:1])[CH2:9]2)=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 1039681,1'-(4-Iodobutylidene)bis[4-fluorobenzene]HCID 212957132-(Methoxymethyl)-1-(trifluoroacetyl)piperazine

Product 1

HCID 212956814-[4,4-Bis(4-fluorophenyl)butyl]-2-(methoxymethyl)-1-(trifluoroacetyl)piperazineYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 6.05 parts of 2-(methoxymethyl)-1-(trifluoroacetyl)piperazine, 5.25 parts of N,N-diethylethananamine and 36 parts of N,N-dimethylformamide were added 11 parts of 1,1'-(4-iodobutylidene)bis[4-fluorobenzene]. Stirring was continued for 4 hours at 75° C. The reaction mixture was cooled and poured onto 400 parts of water. The product was extracted twice with 140 parts of 1,1'-oxybisethane. The combined extracts were dried, filtered and evaporated, yielding 11.5 parts (94%) of 4-[4,4-bis(4-fluorophenyl)butyl]-2-(methoxymethyl)-1-(trifluoroacetyl)piperazine as a residue (intermediate 60).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionThe product was extracted twice with 140 parts of 1,1'-oxybisethane
  3. customThe combined extracts were dried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-837fd5bdd3694a00ac16d99646142825
Source dataset
uspto-grants-1988_08
Patent number
US04766125

Reaction notes

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