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

HRID 242795Notes

Reaction equation

HRID 242795 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]([Cl:25])[C:12]=2[N:11]=1)[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:25][C:24]1[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]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68157799[(S)-1-(4-Chloro-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tertbutyl ester

Product 1

HCID 68158216(S)-1-(4-Chloro-1-phenyl-1H-benzo[D]imidazol-2-YL)ethanamineYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(S)-1-(4-chloro-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tertbutyl ester (1.40 g, 3.76 mmol) in DCM (20 mL) was added TFA (20 mL) and the resulting mixture was stirred at RT for 20 min. Volatiles were removed under reduced pressure and the resulting residue was partitioned between DCM and a saturated solution of NaHCO3. The aqueous layer was further extracted with DCM and the combined organic layers were then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-8% 2M NH3/MeOH in DCM) affording (S)-1-(4-Chloro-1-phenyl-1H-benzoimidazol-2-yl)ethylamine as a white solid (680 mg, 67%). LCMS: RT 2.23 min [M+H]+ 272.1

Workup

  1. customVolatiles were removed under reduced pressure
  2. customthe resulting residue was partitioned between DCM
  3. extractionThe aqueous layer was further extracted with DCM
  4. dry with materialthe combined organic layers were then dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-8% 2M NH3/MeOH in DCM)

Sources & evidence

ORD record
ord-904e1bd60c3442278688b9c3c38cd2af
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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