Trifluoroacetic acid → HCID 68535370, compound

HRID 2180183Notes

Reaction equation

HRID 2180183 reaction equation
C(OC(=O)[N:7]([C:26]1[CH:31]=[CH:30][C:29]([F:32])=[C:28]([F:33])[CH:27]=1)[CH2:8][CH2:9][NH:10][CH2:11][C:12]1([C:19]2[CH:24]=[CH:23][C:22]([I:25])=[CH:21][CH:20]=2)[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:33][C:28]1[CH:27]=[C:26]([NH:7][CH2:8][CH2:9][NH:10][CH2:11][C:12]2([C:19]3[CH:24]=[CH:23][C:22]([I:25])=[CH:21][CH:20]=3)[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH2:17]2)[CH:31]=[CH:30][C:29]=1[F:32]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68532412HCID 68532412, compound

Product 1

HCID 68535370HCID 68535370, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (3,4-difluoro-phenyl)-(2-{[4-(4-iodo-phenyl)-1-methyl-piperidin-4-ylmethyl]-amino}-ethyl)-carbamic acid tert-butyl ester (2.03 g, 3.47 mmol) in CH2Cl2 (25 mL) at 0° C. was added TFA (6 mL, to give a 25% v/v solution). The mixture was stirred and warmed to room temperature for 4 h. The solvent was removed by rotary evaporation and the residue was dissolved in EtOAc (50 mL) and washed with 10% aqueous NaHCO3 (2×50 mL). The organic extracts were dried over sodium sulfate, filtered and concentrated by rotary evaporation to give N-(3,4-difluoro-phenyl)—N′-[4-(4-iodo-phenyl)-1-methyl-piperidin-4-ylmethyl]-ethane-1,2-diamine (1.20 g, 96%) as a white solid.

Workup

  1. customto give a 25% v/v solution)
  2. customThe solvent was removed by rotary evaporation
  3. dissolutionthe residue was dissolved in EtOAc (50 mL)
  4. washwashed with 10% aqueous NaHCO3 (2×50 mL)
  5. dry with materialThe organic extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-a68da550d3e548bdbe4a1f42d9a1600c
Source dataset
uspto-grants-2005_05
Patent number
US06887889B2

Reaction notes

Loading…