Trifluoroacetic acid → (1S)-1-(6-Methyl-1-phenyl-1H-benzimidazol-2-yl)ethan-1-amine

HRID 242810Notes

Reaction equation

HRID 242810 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]=[C:22]([CH3:25])[CH:23]=[CH:24][C:12]=2[N:11]=1)[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:25][C:22]1[CH:23]=[CH:24][C:12]2[N:11]=[C:10]([C@@H:8]([NH2:7])[CH3:9])[N:14]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:13]=2[CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68157577HCID 68157577, compound

Product 1

HCID 68157101(1S)-1-(6-Methyl-1-phenyl-1H-benzimidazol-2-yl)ethan-1-amineYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(S)-1-(6-methyl-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tertbutyl ester (969 mg, 2.76 mmol) in DCM (7.5 mL) was added TFA (2.5 mL) and the mixture was stirred at RT for 20 h. Volatiles were removed under reduced pressure and the resulting residue was dissolved in DCM (30 mL) and washed with a saturated solution of NaHCO3 (40 mL). The two phase system was stirred for 10 min, then the organic layer was dried (Na2SO4) and concentrated in vacuo affording (S)-1-(6-Methyl-1-phenyl-1H-benzoimidazol-2-yl)ethylamine as a brown solid (583 mg, 84%). LCMS: RT 3.02 min [M+H]+ 252.2

Workup

  1. customVolatiles were removed under reduced pressure
  2. dissolutionthe resulting residue was dissolved in DCM (30 mL)
  3. washwashed with a saturated solution of NaHCO3 (40 mL)
  4. stirringThe two phase system was stirred for 10 min
  5. dry with materialthe organic layer was dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ae0559d897ae4e508fc37a3a07cd65ac
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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