Pyridine → HCID 22936218, compound

HRID 1271615Notes

Reaction equation

HRID 1271615 reaction equation
N1C=CC=CC=1.[C:7](Cl)(=[O:15])[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:17]1([N:23]2[CH2:28][CH2:27][CH:26]([NH2:29])[CH2:25][CH2:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)(O)[O-].[Na+]>O1CCCC1>[C:17]1([N:23]2[CH2:24][CH2:25][CH:26]([NH:29][C:7](=[O:15])[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH2:27][CH2:28]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 211933471-Phenylpiperidin-4-amine

Product 1

HCID 22936218HCID 22936218, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Pyridine (24 μL) and phenyl chlorocarbonate (32 μL) were added to a solution of 1-phenyl-4-piperidylamine (35 mg) in tetrahydrofuran (1 mL), and the mixture was stirred at room temperature for 12 hours. The reaction mixture was poured into saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate/chloroform=1/1) to give the title compound (37 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography on silica gel (ethyl acetate/chloroform=1/1)

Sources & evidence

ORD record
ord-4b775339ee004b55b3e5c56ed380e9fb
Source dataset
uspto-grants-2007_04
Patent number
US07205417B2

Reaction notes

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