1,4-Dioxane hydrochloride → 2-(5-Piperidin-4-yl-4h-1,2,4-triazol-3-yl)-pyridine dihydrochloride

HRID 1678756Notes

Reaction equation

HRID 1678756 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[NH:9][N:8]=2)[CH2:3][CH2:2]1.[ClH:18].O1CCOCC1>C(OCC)C.C(#N)C.CO>[ClH:18].[ClH:18].[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[NH:9][N:8]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 178420141HCID 178420141, compound

Product 1

HCID 1784785342-(5-Piperidin-4-yl-4h-1,2,4-triazol-3-yl)-pyridine dihydrochloride

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×HCID 6342AcetonitrileSolvent

Procedure

This material (2.68 g, 8.14 mmol) was suspended in 4 N HCl/dioxane. The stoppered reaction mixture was stirred at room temperature for 16 hours and then diluted with diethyl ether. The solids were isolated by filtration and the hygroscopic solid was digested in acetonitrile. This solid was isolated by filtration and partially dissolved in hot methanol. Upon cooling and addition of some ethyl ether to the solution 2-(3-piperidin-4-yl-1H-1,2,4-triazol-5-yl)pyridine slowly precipitated as the dihydrochloride salt. 1H NMR (500 MHz, DMSO-d6): δ 9.10 (1H, br s), 8.92 (1H, br s), 8.73 (1H, d, J=4.9 Hz), 8.10-8.20 (2H, m), 7.64 (1H, t, J=5.7 Hz), 3.33 (2H, br d, J=12.7 Hz), 3.16 (1H, m), 3.05 (2H, br q, J=11.9 Hz, J=21.8 Hz), 2.18 (2H, br d, J=11.5 Hz), 1.99 (2H, br q, j=11.0 Hz, J=22.2 Hz): m/e (m+1): 230.3.

Workup

  1. customThe stoppered reaction mixture
  2. customThe solids were isolated by filtration
  3. customThis solid was isolated by filtration
  4. temperatureUpon cooling
  5. customslowly precipitated as the dihydrochloride salt

Sources & evidence

ORD record
ord-bdc58db9c08f483d80c1cc1e750b67a1
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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