Potassium Hydroxide → tert-butyl 4-(1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate

HRID 1685164Notes

Reaction equation

HRID 1685164 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[NH:15][CH:16]=[CH:17][N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].Br[CH2:22][CH2:23][O:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][O:26]1>CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[N:18]([CH2:22][CH2:23][O:24][CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][O:26]3)[CH:17]=[CH:16][N:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 17840015tert-butyl 4-(1H-imidazol-2-yl)piperidine-1-carboxylate

Product 1

HCID 67112320tert-butyl 4-(1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylateYield 97%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Add 4-(1H-imidazol-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (40 g; 0.16 mol; 1.0 equiv), powdered KOH (35.6 g; 0.64 mol; 4.0 equiv), 2-(2-bromo-ethoxy)-tetrahydropyran (66.2 g; 0.32 mol; 2.0 equiv) to DMSO (250 mL) and stir at RT for 2 h. Quench the reaction with water and extract with EA. Evaporate the organic layer to give the title compound (58 g; 97%).

Workup

  1. customQuench
  2. customthe reaction with water
  3. extractionextract with EA
  4. customEvaporate the organic layer

Sources & evidence

ORD record
ord-06d91fc0a7b34cb1a995d8bd4e6c9f40
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

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