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

HRID 604989Notes

Reaction equation

HRID 604989 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): 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-4bcc86d9414348618f38f5f12ec8eead
Source dataset
uspto-grants-2011_03
Patent number
US07910561B2

Reaction notes

Loading…