Potassium Carbonate → (S)-1-(4'-Chloro-biphenyl-2-ylmethyl)-2-methyl-piperidin-4-one

HRID 2406230Notes

Reaction equation

HRID 2406230 reaction equation
Cl.[CH3:2][C@H:3]1[CH2:8][C:7](=[O:9])[CH2:6][CH2:5][NH:4]1.C([O-])([O-])=O.[K+].[K+].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH2:29]I)=[CH:19][CH:18]=1>C(#N)C>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH2:29][N:4]2[CH2:5][CH2:6][C:7](=[O:9])[CH2:8][C@@H:3]2[CH3:2])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 670542934'-Chloro-2-(iodomethyl)biphenylHCID 67980815(S)-2-Methylpiperidin-4-one hydrochloride

Product 1

HCID 67980706(S)-1-(4'-Chloro-biphenyl-2-ylmethyl)-2-methyl-piperidin-4-oneYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

(S)-2-Methyl-piperidin-4-one hydrochloride (100 mg, 0.67 mmol) was combined with K2CO3 (554 mg, 4.0 mmol) in acetonitrile (5.0 mL) and stirred for 15 minutes. 4′-Chloro-2-(iodomethyl)biphenyl (220 mg, 0.668 mmol) was added, and the resulting mixture was heated to 70° C. and stirred for 16 hours. The reaction was cooled to room temperature, filtered, and concentrated. The crude residue was purified by flash chromatography on silica gel (heptanes/EtOAc gradient) to afford the title compound as an off-white solid (178 mg, 85% yield). MS (ESI) m/e (M+H+): 313.8

Workup

  1. stirringstirred for 16 hours
  2. temperatureThe reaction was cooled to room temperature
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by flash chromatography on silica gel (heptanes/EtOAc gradient)

Sources & evidence

ORD record
ord-2b5c3c16db384efd89302892ba4eec9a
Source dataset
uspto-grants-2014_08
Patent number
US08809352B2

Reaction notes

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