Trifluoroacetic acid → 3-(3,5-Dichloro-phenyl)-1-[4-(4-iodo-phenyl)-piperidin-4-ylmethyl]-1-methyl-urea

HRID 2180189Notes

Reaction equation

HRID 2180189 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([CH2:21][N:22]([CH3:34])[C:23]([NH:25][C:26]2[CH:31]=[C:30]([Cl:32])[CH:29]=[C:28]([Cl:33])[CH:27]=2)=[O:24])([C:14]2[CH:19]=[CH:18][C:17]([I:20])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:33][C:28]1[CH:27]=[C:26]([NH:25][C:23](=[O:24])[N:22]([CH2:21][C:11]2([C:14]3[CH:15]=[CH:16][C:17]([I:20])=[CH:18][CH:19]=3)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[CH3:34])[CH:31]=[C:30]([Cl:32])[CH:29]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68534877HCID 68534877, compound

Product 1

HCID 224903673-(3,5-Dichloro-phenyl)-1-[4-(4-iodo-phenyl)-piperidin-4-ylmethyl]-1-methyl-ureaYield 104.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[3-(3,5-dichloro-phenyl)-1-methyl-ureidomethyl]-4-(4-iodo-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (0.218 g, 0.35 mmol) in CH2Cl2 (4.5 mL) at 0° C. was added TFA (1.5 mL, to give a 25% v/v solution). The reaction mixture was warmed to room temperature and stirred for 4 h. The solvent was removed by rotary evaporation and the residue was dissolved in EtOAc (25 mL) and washed with 10% aqueous NaHCO3 (2×25 mL). The organic extracts were dried over anhydrous Na2SO4, filtered and concentrated by rotary evaporation to give 3-(3,5-dichloro-phenyl)-1-[4-(4-iodo-phenyl)-piperidin-4-ylmethyl]-1-methyl-urea (˜0.19 g, 100%).

Workup

  1. customto give a 25% v/v solution)
  2. customThe solvent was removed by rotary evaporation
  3. dissolutionthe residue was dissolved in EtOAc (25 mL)
  4. washwashed with 10% aqueous NaHCO3 (2×25 mL)
  5. dry with materialThe organic extracts were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-fa103b52fbd5491194ff4976bd543837
Source dataset
uspto-grants-2005_05
Patent number
US06887889B2

Reaction notes

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