Potassium Carbonate → HCID 24957018, compound

HRID 1665205Notes

Reaction equation

HRID 1665205 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13]([CH3:14])=[N:12][C:11]([OH:15])=[N:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>CO.O>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13]([CH3:14])=[N:12][C:11]([O:15][CH2:24][CH2:25][N:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)=[N:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 178433517HCID 178433517, compound

Product 1

HCID 24957018HCID 24957018, compoundYield 20.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

1-(3,4-Dichlorophenyl)-5-methyl-1H-1,2,4-triazole-3-ol (0.41 mmol) was dissolved in methanol (150 mL) at room temperature. A solution of potassium carbonate in water (30 mL) was added dropwise until pH 9. After 15 min under stirring a solution of 1-(2 chloroethyl) piperidine hydrochloride (0.62 mmol) in water (100 mL) was added. The reaction was stirred at room temperature overnight. The methanol was evaporated and after extraction with CH2Cl2 the organic layer was dried over MgSO4 then evaporated and finally purified by chromatography in silica gel to give 1-{2-[1-(3,4-dichlorophenyl)-5-methyl-1H-1,2,4-triazol-3-yloxy]ethyl}piperidine (0.03 g, yield 20%) as a dark orange oil. H1NMR (300 MHz, CDCl3, 25° C.) δ: 7.53 (d, J=2.4 Hz, 1H); 7.48 (d, J=8.6 Hz, 1H); 7.23 (dd, J=2.4 Hz, 1H); 4.33 (t, J=5.9 Hz, 2H); 2.71 (t, J=5.9 Hz, 2H); 2.44 (t, J=4.9 Hz, 4H); 2.40 (s, 3H); 1.51 (q, J=5.5 Hz, 4H); 1.34 (m, 2H) ppm. EM (ES+) m/z=355 (100%) [M+H]+. C16H20Cl2N4O (355.26) calc. C, 54.09%; H, 5.67%; N, 15.77%. found C, 53.80%; H, 5.72%; N, 15.48%.

Workup

  1. additionwas added
  2. customThe methanol was evaporated
  3. extractionafter extraction with CH2Cl2 the organic layer
  4. dry with materialwas dried over MgSO4
  5. customthen evaporated
  6. customfinally purified by chromatography in silica gel

Sources & evidence

ORD record
ord-179c0e7cb43b4519a1292979325c8554
Source dataset
uspto-grants-2011_10
Patent number
US08039497B2

Reaction notes

Loading…