Potassium Carbonate → Benzyl 4-({3-[hydroxy(diphenyl)methyl]-1H-1,2,4-triazol-1-yl}methyl)piperidine-1-carboxylate

HRID 2383382Notes

Reaction equation

Br[CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:5][CH2:4]1.[C:19]1([C:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:27]2[N:31]=[CH:30][NH:29][N:28]=2)[OH:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[OH:26][C:25]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:27]1[N:31]=[CH:30][N:29]([CH2:2][CH:3]2[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:10])[CH2:5][CH2:4]2)[N:28]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Benzyl 4-(bromomethyl)piperidine-1-carboxylate (5 g, 16 mmol) was dissolved in dimethylformamide (40 ml) and diphenyl-(1H-[1,2,4]triazol-3-yl)-methanol (Tetrahedron: Asymmetry, 8(9), 1491-1500; 1997; 3.35 g, 13.65 mmol) added, followed by potassium carbonate (3.69 g, 26.7 mmol). After stirring at 70° C. for 18 hours the solvent was removed in vacuo, and the residue partitioned between ethyl acetate (150 ml) and water (150 mL). The organic layer was separated, dried over magnesium sulphate, filtered and the solvent removed in vacuo to furnish the title compound as a white solid in 81% yield, 5.2 g.

Workup

customwas removed in vacuo
customthe residue partitioned between ethyl acetate (150 ml) and water (150 mL)
customThe organic layer was separated
dry with materialdried over magnesium sulphate
filtrationfiltered
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-d621d1001885485288657c889dd2af88
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263623B2

Reaction notes

Loading…