1-(3-(Trifluoromethyl)phenyl)piperazine → HCID 178516902, compound

HRID 1788911Notes

Reaction equation

HRID 1788911 reaction equation
[O:1]1[CH:11]2[CH:2]1[C:3](=[O:13])[C:4]1[C:9]([C:10]2=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=1.[F:14][C:15]([F:29])([F:28])[C:16]1[CH:17]=[C:18]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:19]=[CH:20][CH:21]=1>C(O)C>[OH:1][C:11]1[C:10](=[O:12])[C:9]2[C:4]([C:3](=[O:13])[C:2]=1[N:25]1[CH2:24][CH2:23][N:22]([C:18]3[CH:19]=[CH:20][CH:21]=[C:16]([C:15]([F:28])([F:29])[F:14])[CH:17]=3)[CH2:27][CH2:26]1)=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

4

Reactant 2

HCID 42961-(3-(Trifluoromethyl)phenyl)piperazineHCID 858442,3-Epoxy-2,3-dihydro-1,4-naphthoquinone

Product 1

HCID 178516902HCID 178516902, compoundYield 29.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.74 g of 2,3-epoxy-2,3-dihydro-1,4-naphthoquinone and 2.30 g of N-[3-(trifluoromethyl)phenyl]piperazine in 100 ml of absolute ethanol was stirred for 20 hours, then evaporated. The residue was dissolved in dichloromethane, filtered through hydrous magnesium silicate and then chromatographed on silica gel, eluting with hexane:ethyl acetate (4:1), giving 1.2 g of the desired product, mp 167°-169° C.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in dichloromethane
  3. filtrationfiltered through hydrous magnesium silicate
  4. customchromatographed on silica gel
  5. washeluting with hexane:ethyl acetate (4:1)

Sources & evidence

ORD record
ord-ce5069d4005549b6a217e8c95207166c
Source dataset
uspto-grants-1987_08
Patent number
US04686220

Reaction notes

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