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

HRID 1761950Notes

Reaction equation

HRID 1761950 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-342f8cfd6370481eaf6c31e89b2515b4
Source dataset
uspto-grants-1989_05
Patent number
US04829089

Reaction notes

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