Water → HCID 22380639, compound

HRID 1006441Notes

Reaction equation

HRID 1006441 reaction equation
[NH2:1][CH2:2][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.Cl[C:22]([O:24][CH2:25][CH3:26])=[O:23].C(N(CC)CC)C.O>ClCCl>[CH2:12]([O:11][C:9]([N:6]1[CH2:7][CH2:8][C:3]([CH2:2][NH:1][C:22]([O:24][CH2:25][CH3:26])=[O:23])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[CH2:4][CH2:5]1)=[O:10])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 22380627HCID 22380627, compound

Product 1

HCID 22380639HCID 22380639, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Subsequently, the obtained 4-aminomethyl-1-(ethoxycarbonyl)-4-(2-methylphenyl)piperidine was dissolved in dichloromethane (10 ml), added with ethyl chloroformate (0.18 ml) and triethylamine (0.26 ml) and stirred at room temperature for 30 minutes. The reaction mixture was added with water (10 ml), and the layers were separated. Then, the aqueous layer was further extracted 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=2:1) to obtain 372 mg of the title compound. Yield: 51% (for the two steps).

Workup

  1. customthe layers were separated
  2. extractionThen, the aqueous layer was further extracted with dichloromethane (10 ml)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-84cc4547a02b4fc3a73e19cfc547d604
Source dataset
uspto-grants-2004_09
Patent number
US06790854B2

Reaction notes

Loading…