Ammonium Chloride → HCID 178420116, compound

HRID 419702Notes

Reaction equation

HRID 419702 reaction equation
O=[C:2]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:3][NH:4][C:5]([CH:7]1[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]1)=O.[NH4+:26].[Cl-]>C(O)C>[C:20]1([C:2]2[N:26]=[C:5]([CH:7]3[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]3)[NH:4][CH:3]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 58270705Tert-butyl 4-[(2-oxo-2-phenylethyl)carbamoyl]piperidine-1-carboxylate

Product 1

HCID 178420116HCID 178420116, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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. temperatureMicrowave heat
  2. additionadd silica gel (5 mL)
  3. concentrationconcentrate the mixture in vacuo
  4. customPurify the residue by silica gel chromatography (80 g RediSep column
  5. washelute with a gradient of 0% through 100% CMA/methylene chloride over 60 min

Sources & evidence

ORD record
ord-5f8b2bdf243540cabc6864a559303136
Source dataset
uspto-grants-2012_01
Patent number
US08093383B2

Reaction notes

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