Hydrochloric Acid → HCID 178477953, compound

HRID 419703Notes

Reaction equation

HRID 419703 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:18]>C(Cl)Cl>[ClH:18].[C:1]1([C:7]2[N:8]=[C:9]([CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[NH:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178420116HCID 178420116, compound

Product 1

HCID 178477953HCID 178477953, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Microwave heat a mixture of tert-butyl 4-(2-oxo-2-phenylethylcarbamoyl)-piperidine-1-carboxylate (1.0 g, 2.88 mmol) and NH4Cl (0.462 g, 8.65 mmol) in ethanol (12 mL) at 300 W, 160° C., and 14 bar for 11 h in a Personal Chemistry microwave. Cool the mixture to room temperature, add silica gel (5 mL), and concentrate the mixture in vacuo. Purify the residue by silica gel chromatography (80 g RediSep column, elute with a gradient of 0% through 100% CMA/methylene chloride over 60 min, 60 mL/min) to provide 4-(4-phenyl-1H-imidazol-2-yl)piperidine (0.418 g, 64%) as an off-white solid. Add 4-(4-phenyl-1H-imidazol-2-yl)piperidine (0.060 g, 0.26 mmol) to methylene chloride (15 mL) and concentrated hydrochloric acid (28 μL). Stir the mixture for 45 min, then concentrate the mixture in vacuo to provide 4-(4-phenyl-1H-imidazol-2-yl)piperidine hydrochloride (0.070 g, 99%).

Workup

  1. concentrationconcentrate the mixture in vacuo

Sources & evidence

ORD record
ord-5fd14016b02a4859a5b5f80c92f04817
Source dataset
uspto-grants-2012_01
Patent number
US08093383B2

Reaction notes

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