p-Toluenesulfonic acid → HCID 21098257, compound

HRID 1593023Notes

Reaction equation

HRID 1593023 reaction equation
CN(C=[N:5][N:6]=[CH:7][N:8]([CH3:10])[CH3:9])C.[CH2:11]([N:18]1[CH2:23][CH2:22]C(N)[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:11]([N:18]1[CH2:23][CH2:22][CH:10]([N:8]2[CH:7]=[N:6][N:5]=[CH:9]2)[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 4158521-Benzyl-4-piperidylamineHCID 3725062N,N'-Bis(dimethylaminomethylene)hydrazine

Product 1

HCID 21098257HCID 21098257, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1,2-bis[(dimethylamino)methylene]hydrazine (660 mg) in toluene (10 ml) was added 1-benzylpiperidin-4-amine (0.8 ml) and p-toluenesulfonic acid (75 mg) and the resulting mixture was stirred at room temperature for 18 hours. The reaction mixture was refluxed for 8 hours and then evaporated to dryness. The residue was purified by chromatography on silica eluting with a gradient of methanol/ethyl acetate to give 1-benzyl-4-(4H-1,2,4-triazol-4-yl)piperidine. Yield 220 mgs. NMR (d6 DMSO): 2.0 (m, 4H), 2.1 (m, 2H), 2.9 (m, 2H), 3.5 (s, 2H), 4.2 9m, 1H), 7.35 (m, 5H), 8.65 (s, 2H).

Workup

  1. temperatureThe reaction mixture was refluxed for 8 hours
  2. customevaporated to dryness
  3. customThe residue was purified by chromatography on silica eluting with a gradient of methanol/ethyl acetate

Sources & evidence

ORD record
ord-c8902fbce9384c70b2a64eb4d0159242
Source dataset
uspto-grants-2007_11
Patent number
US07294636B2

Reaction notes

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