Trifluoroacetic acid → (S)-1-(4-Methyl-1-phenyl-1H-benzo[D]imidazol-2-YL)ethanamine

HRID 242777Notes

Reaction equation

HRID 242777 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:13]2[CH:21]=[CH:22][CH:23]=[C:24]([CH3:25])[C:12]=2[N:11]=1)[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:25][C:24]1[C:12]2[N:11]=[C:10]([C@@H:8]([NH2:7])[CH3:9])[N:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:13]=2[CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 68157102[(S)-1-(4-methyl-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tertbutyl ester

Product 1

HCID 68157022(S)-1-(4-Methyl-1-phenyl-1H-benzo[D]imidazol-2-YL)ethanamineYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(S)-1-(4-methyl-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tertbutyl ester (380 mg, 1.08 mmol) in DCM (5 mL) was added TFA (1 mL) and the mixture was stirred at RT for 3 h. Additional TFA (0.5 mL) was added and stirring was continued for 30 min. Volatiles were then removed under reduced pressure and the residue was then dissolved in a small amount of DCM and loaded onto an SCX-2 cartridge which was initially washed with 10% MeOH in DCM. The product was eluted with 2M NH3/MeOH affording (S)-1-(4-Methyl-1-phenyl-1H-benzoimidazol-2-yl)ethylamine as a brown solid (222 mg, 82%). LCMS: RT 2.16 [M-NH2]+ 235.1

Workup

  1. stirringstirring
  2. waitwas continued for 30 min
  3. customVolatiles were then removed under reduced pressure
  4. dissolutionthe residue was then dissolved in a small amount of DCM
  5. washwas initially washed with 10% MeOH in DCM
  6. washThe product was eluted with 2M NH3/MeOH

Sources & evidence

ORD record
ord-0b89eab8a0a24ab2b2cc380514b33593
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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