Hydrochloric Acid → HCID 22380627, compound

HRID 895640Notes

Reaction equation

HRID 895640 reaction equation
[C:1]([C:3]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:4]1)#[N:2].Cl>C(O)C.[Pd]>[NH2:2][CH2:1][C:3]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22380599HCID 22380599, compound

Product 1

HCID 22380627HCID 22380627, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-Cyano-1-(ethoxycarbonyl)-4-(2-methylphenyl)piperidine (504 mg) was dissolved in ethanol (10 ml), added with 10% palladium/carbon (500 mg) and 5 N aqueous hydrochloric acid (0.74 ml) and stirred at room temperature for 15 hours under hydrogen gas pressure (30 psi) by using the Parr apparatus. After insoluble matters were removed by filtration, ethanol was evaporated under reduced pressure. The residue was added with dichloromethane (50 ml) and adjusted to pH 9 with saturated aqueous sodium hydrogencarbonate. The organic layer was separated, and the aqueous layer was further extracted with dichloromethane (50 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure to obtain 4-aminomethyl-1-(ethoxycarbonyl)-4-(2-methylphenyl)piperidine.

Workup

  1. customAfter insoluble matters were removed by filtration, ethanol
  2. customwas evaporated under reduced pressure
  3. additionThe residue was added with dichloromethane (50 ml)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was further extracted with dichloromethane (50 ml)
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-bc2bac8ea7fa4352acd0e02a511a3322
Source dataset
uspto-grants-2005_07
Patent number
US06916822B2

Reaction notes

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