Water → HCID 22380577, compound

HRID 895636Notes

Reaction equation

HRID 895636 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][CH2:11]1.Cl[C:22](Cl)([O:24]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.O>ClCCl>[CH2:19]([O:18][C:16]([N:13]1[CH2:12][CH2:11][CH:10]([N:9]2[C:3]3[C:4]([CH3:8])=[CH:5][CH:6]=[CH:7][C:2]=3[NH:1][C:22]2=[O:24])[CH2:15][CH2:14]1)=[O:17])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 94429TriphosgeneHCID 22380762HCID 22380762, compound

Product 1

HCID 22380577HCID 22380577, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[(2-Amino-6-methylphenyl)amino]-1-ethoxycarbonylpiperidine (75.2 mg) was dissolved in dichloromethane (1.5 ml), added with triphosgene (80.5 mg) and triethylamine (76 μl) and stirred at room temperature for 2 hours. The reaction mixture was added with water (5 ml) and extracted twice with ethyl acetate (5 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by preparative thin layer silica gel column chromatography (developing solvent: hexane:ethyl acetate=1:1) to obtain 59.1 mg of the title compound. Yield: 72%.

Workup

  1. extractionextracted twice with ethyl acetate (5 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 preparative thin layer silica gel column chromatography (developing solvent: hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-b0d8dc429a7144eaab6578399310f51c
Source dataset
uspto-grants-2005_07
Patent number
US06916822B2

Reaction notes

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