1-(3-(Trifluoromethyl)phenyl)piperazine → HCID 15592121, compound

HRID 2417609Notes

Reaction equation

HRID 2417609 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.C[O:18][C:19]1[C:20](=O)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1>CO>[F:16][C:2]([F:1])([F:15])[C:3]1[CH:4]=[C:5]([N:9]2[CH2:14][CH2:13][N:12]([C:25]3[C:19](=[O:18])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 42961-(3-(Trifluoromethyl)phenyl)piperazineHCID 165462-Methoxy-2,4,6-cycloheptatrien-1-one

Product 1

HCID 15592121HCID 15592121, compoundYield 122.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-(3-trifluoromethylphenyl)-piperazine (2.3 g) and 2-methoxy-2,4,6-cycloheptatrien-1-one (2.0 g) in methanol (50 ml) was refluxed for 24 hr and evaporated. The residue was chromatographed on silica gel (100 g) using ethyl acetate. The eluates were evaporated and crystallized from ethyl acetate-benzene to give the title compound (4.08 g): mp 112°-114° C.; ir (CHCl3) 1570 cm-1 ; uv max (MeOH)350 (ε=10575) and 256 nm (ε=31730); nmr (CDCl3)δ 3.5 (m, 8H) and 7.0 (m, 9H); and Anal. Calcd for C18H17F3N2O: C, 64.66% H, 5.12% N, 8.38% and Found: C, 64.84% H, 5.17% N, 8.54%.

Workup

  1. temperaturewas refluxed for 24 hr
  2. customevaporated
  3. customThe residue was chromatographed on silica gel (100 g)
  4. customThe eluates were evaporated
  5. customcrystallized from ethyl acetate-benzene

Sources & evidence

ORD record
ord-c55050bbf9584b97b264c91f4723e837
Source dataset
uspto-grants-1984_09
Patent number
US04469694

Reaction notes

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