1-(1-Naphthyl)piperazine → HCID 19872074, compound

HRID 329415Notes

Reaction equation

HRID 329415 reaction equation
Cl[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[N:12][S:13][CH:14]=2)=[CH:6][CH:5]=1.[C:15]1([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1.C(N(C(C)C)CC)(C)C.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>CC(CC(C)C)=O>[S:13]1[CH:14]=[CH:10][N:11]=[N:12]1.[C:15]1([N:25]2[CH2:30][CH2:29][N:28]([CH2:2][CH2:3][C:4]3[CH:9]=[CH:8][C:7]([C:10]4[N:11]=[N:12][S:13][CH:14]=4)=[CH:6][CH:5]=3)[CH2:27][CH2:26]2)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 5

HCID 13421-(1-Naphthyl)piperazineHCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 14726979HCID 14726979, compound

Product 1

HCID 19872074HCID 19872074, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

To a 100 ml round-bottomed flask equipped with condenser and N2 inlet were added 0.64 g (2.83 mmol) (4-(4-(2-chloroethyl)phenyl)-1,2,3-thiadiazole, 0.60 g (2.83 mmol) N-(1-naphthyl)piperazine, 0.49 ml (2.83 mmol) diisopropylethylamine, 0.60 g (5.66 mmol) sodium carbonate, 2 mg sodium iodide, and 20 ml methylisobutylketone. The reaction was refluxed 4 days, cooled, and evaporated. The residue was taken up in ethyl acetate, washed with water and brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using methylene chloride/ethyl acetate as eluent and the product fractions dissolved in ethyl acetate and precipitated with ethyl acetate saturated with HCl. The precipitate was filtered and dried to give a solid, 0.62 g (50%), m.p. 286-289° C. NMR (DMSO-d6 and TFA): 3.6 (m, 2H), 3.9 (m, 2H), 4.4-4.7 (m, 8H), 7.5-8.2 (m, 11H), 9.42 (s, 1H).

Workup

  1. customTo a 100 ml round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction was refluxed 4 days
  3. temperaturecooled
  4. customevaporated
  5. washwashed with water and brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe residue was chromatographed on silica gel
  9. dissolutionthe product fractions dissolved in ethyl acetate
  10. customprecipitated with ethyl acetate saturated with HCl
  11. filtrationThe precipitate was filtered
  12. customdried
  13. customto give a solid, 0.62 g (50%), m.p. 286-289° C

Sources & evidence

ORD record
ord-47338a779c2d489ebbdce5fb7932c1c0
Source dataset
uspto-grants-1990_01
Patent number
US04891375

Reaction notes

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