Water → HCID 22380599, compound

HRID 1006439Notes

Reaction equation

HRID 1006439 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([C:21]#[N:22])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[CH2:10][CH2:9]1)C1C=CC=CC=1.Cl[C:24]([O:26][CH2:27][CH3:28])=[O:25].C(=O)([O-])O.[K+].O>ClCCl>[C:21]([C:11]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[CH2:12][CH2:13][N:8]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:9][CH2:10]1)#[N:22]

Participants

6

Reactant 4

HCID 962WaterHCID 10928Ethyl chloroformateHCID 516893Potassium BicarbonateHCID 22380616HCID 22380616, compound

Product 1

HCID 22380599HCID 22380599, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Benzyl-4-cyano-4-(2-methylphenyl)piperidine (406 mg) was dissolved in dichloromethane (8 ml), added with ethyl chloroformate (0.16 ml) and potassium hydrogencarbonate (168 mg) and stirred at room temperature for 24 hours. The reaction mixture was added with water (10 ml) and extracted twice with dichloromethane (10 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=5:1→4:1) to obtain 381 mg of the title compound. Yield: 100%.

Workup

  1. extractionextracted twice with dichloromethane (10 ml)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=5:1→4:1)

Sources & evidence

ORD record
ord-3c8cbe44a31b480fbc7a4651fc22ae5a
Source dataset
uspto-grants-2004_09
Patent number
US06790854B2

Reaction notes

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