Trifluoroacetic acid → (S)-1-(1-Phenyl-1H-benzoimidazol-2-yl)propylamine

HRID 242806Notes

Reaction equation

HRID 242806 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:11]1[N:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:14]2[CH:22]=[CH:23][CH:24]=[CH:25][C:13]=2[N:12]=1)[CH2:9][CH3:10])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:16]1([N:15]2[C:14]3[CH:22]=[CH:23][CH:24]=[CH:25][C:13]=3[N:12]=[C:11]2[C@@H:8]([NH2:7])[CH2:9][CH3:10])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68157215[(S)-1-(1-Phenyl-1H-benzoimidazol-2-yl)propyl]carbamic acid tertbutyl ester

Product 1

HCID 68157690(S)-1-(1-Phenyl-1H-benzoimidazol-2-yl)propylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(S)-1-(1-phenyl-1H-benzoimidazol-2-yl)propyl]carbamic acid tertbutyl ester (1.76 g) in DCM (10 mL) was added TFA (7.5 mL) and the mixture was stirred at RT for 4 h. Volatiles were removed under reduced pressure and the resulting residue was dissolved in DCM and washed with a saturated solution of NaHCO3. The two phase system was stirred for 20 min, then the organic layer was dried (Na2SO4) and concentrated in vacuo affording (S)-1-(1-Phenyl-1H-benzoimidazol-2-yl)propylamine as a brown oil (1.1 g, 81% over three steps). LCMS: RT 2.02 min [M+H]+ 252.2

Workup

  1. customVolatiles were removed under reduced pressure
  2. dissolutionthe resulting residue was dissolved in DCM
  3. washwashed with a saturated solution of NaHCO3
  4. stirringThe two phase system was stirred for 20 min
  5. dry with materialthe organic layer was dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-263ebe1107be4b4fb40ec599ca9a8b4f
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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